OLA Old Mutual/Claymore Long-Short Fund Old Mutual/Claymore Long-Short Fund Common Shares of Beneficial Interest

UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

FORM N-CSR

CERTIFIED SHAREHOLDER REPORT OF REGISTERED MANAGEMENT INVESTMENT COMPANIES

Form N-CSR is to be used by management investment companies to file reports with the Commission not later than 10 days after the transmission to stockholders of any report that is required to be transmitted to stockholders under Rule 30e-1 under the Investment Company Act of 1940 (17 CFR 270.30e-1). The Commission may use the information provided on Form N-CSR in its regulatory, disclosure review, inspection, and policymaking roles.

A registrant is required to disclose the information specified by Form N-CSR, and the Commission will make this information public. A registrant is not required to respond to the collection of information contained in Form N-CSR unless the Form displays a currently valid Office of Management and Budget ("OMB") control number. Please direct comments concerning the accuracy of the information collection burden estimate and any suggestions for reducing the burden to Secretary, Securities and Exchange Commission, 450 Fifth Street, NW, Washington, DC 20549-0609. The OMB has reviewed this collection of information under the clearance requirements of 44 U.S.C. Section 3507.

ITEM 1. REPORTS TO STOCKHOLDERS.

The registrant's annual report transmitted to shareholders pursuant to Rule 30e-1 under the Investment Company Act of 1940, as amended (the "Investment Company Act") is as follows:

 ANNUAL REPORT OLD MUTUAL/CLAYMORE LONG-SHORT FUND | OLA
December 31, 2008

 [PHOTO]

Logo: OLD MUTUAL | Asset Management

 Logo: CLAYMORE(SM)

 WWW.CLAYMORE.COM/OLA
 ... YOUR COURSE TO THE LATEST,
 MOST UP-TO-DATE INFORMATION ABOUT THE
 OLD MUTUAL/CLAYMORE LONG-SHORT FUND

 OLA Old Mutual/
 LISTED Claymore
 NYSE(R) Long-Short Fund

Logo: OLD MUTUAL | Asset Management

 Logo: CLAYMORE(SM)

There can be no assurance the Fund will achieve its investment objective.
The value of the Fund will fluctuate with the value of the Underlying securities. Historically, closed-end funds often trade at a discount to their net asset value.

NOT FDIC INSURED o NOT BANK-GUARANTEED o MAY LOSE VALUE

The shareholder report you are reading right now is just the beginning of the story. Online at WWW.CLAYMORE.COM/OLA, you will find:

o Daily, weekly and monthly data on share prices, distributions and more

o Portfolio overviews and performance analyses

o Announcements, press releases and special notices

o Fund and adviser contact information

Analytic Investors, LLC and Claymore are continually updating and expanding shareholder information services on the Fund's website, in an ongoing effort to provide you with the most current information about how your Fund's assets are managed, and the results of our efforts. It is just one more way we are working to keep you better informed about your investment in the Fund.

2 | Annual Report | December 31, 2008

OLA | Old Mutual/Claymore Long-Short Fund

Dear SHAREHOLDER |

We thank you for your investment in the Old Mutual/Claymore Long-Short Fund (the "Fund"). This report covers the Fund's performance for the fiscal year ended December 31, 2008. This has been an extraordinarily difficult time for all investors, and we are disappointed to report that the Fund's return was negative for the period.

The Fund's investment objective is to provide a high level of current income and gains with a secondary objective of long-term capital appreciation. The Fund seeks to achieve these objectives by investing in a diversified portfolio of common stocks and other equity securities utilizing a long/short strategy and opportunistically employing a strategy of writing (selling) calls on equity indices and, to a lesser extent, on individual securities held in the Fund's port-folio. The Fund also seeks to enhance returns through an asset allocation strategy that involves purchasing or selling futures contracts on U.S. or foreign securities indices, foreign currencies and other assets.

Analytic Investors, LLC ("Analytic") is the Fund's investment sub-adviser. The firm, established in 1970, is a majority-owned subsidiary of Old Mutual (US) Holdings Inc., more commonly known as Old Mutual Asset Management. Analytic specializes in the creation and continuous management of optioned-equity and optioned-debt portfolios for mutual funds, foundations, insurance companies, endowments, profit-sharing plans, funds of hedge funds, and individual investors. As of December 31, 2008,Analytic managed or supervised approximately $8.7 billion in assets.

We believe that the Fund provides shareholders with the potential to outperform the S&P 500 Index over full market cycles through its unique multi-strategy approach to investing. Analytic has employed the Fund's strategy for nearly three decades in other investment products for institutional and retail investors. While the Fund's options overlay has similarities to a covered call fund, the Fund's long/short equity security selection and its asset allocation makes it different. We believe that this multi-strategy approach provides opportunities unavailable in a traditional covered call fund.

All Fund returns cited--whether based on net asset value ("NAV") or market price--assume the reinvestment of all distributions. For the 12 months ended December 31, 2008, the Fund provided a total return based on market price of -39.88% and a total return based on NAV of -35.09%. As of December 31, 2008, the Fund's market price of $7.98 per share represented a discount of 22.07% to its NAV of $10.24 per share. Past performance is not a guarantee of future results.

The market value of the Fund's shares fluctuates from time to time, and it may be higher or lower than the Fund's NAV. The current discount to NAV may provide an opportunity for suitable investors to purchase shares of the Fund below the market value of the securities in the underlying portfolio. We believe that, over the long term, the progress of the NAV will be reflected in the market price return to shareholders.

Annual Report | December 31, 2008 | 3

OLA | Old Mutual/Claymore Long-Short Fund | DEAR SHAREHOLDER continued

We encourage shareholders to consider the opportunity to reinvest their distributions from the Fund through the Dividend Reinvestment Plan ("DRIP"), which is described in detail on page 28 of the Fund's annual report. When shares trade at a discount to NAV, the DRIP takes advantage of the discount by reinvesting the quarterly dividend distribution in common shares of the Fund purchased in the market at a price less than NAV. Conversely, when the market price of the Fund's common shares is at a premium above NAV, the DRIP reinvests participants' dividends in newly-issued common shares at NAV, subject to an IRS limitation that the purchase price cannot be more than 5% below the market price per share. The DRIP provides a cost-effective means to accumulate additional shares and enjoy the benefits of compounding returns over time. Since the Fund endeavors to maintain a steady quarterly distribution rate, the DRIP plan effectively provides an income averaging technique, which allows shareholders to accumulate a larger number of Fund shares when the market price is depressed than when the price is higher.

The Fund provided investors with consistent quarterly distributions of $0.40 per share during 2008. This represents an annualized distribution rate of 20.05% based upon the closing market price of $7.98 per share on December 31, 2008. Each of the distributions was accompanied by a letter detailing the expected characterization of the distribution for tax purposes. These letters are also posted on the Fund's website.

To learn more about the Fund's performance and investment strategy, we encourage you to read the Questions & Answers section of the report, which begins on page
5. You will find information about Analytic's investment philosophy and discipline, its views on the market environment and how it structured the Fund's portfolio based on its views.

We appreciate your investment and look forward to serving your investment needs in the future. For the most up-to-date information on your investment, please visit the Fund's website at www.claymore.com/ola.

Sincerely,

/s/ J. Thomas Futrell
-------------------------
J. Thomas Futrell
Old Mutual/Claymore Long-Short Fund

4 | Annual Report | December 31, 2008

OLA | Old Mutual/Claymore Long-Short Fund

QUESTIONS & ANSWERS |

DENNIS M. BEIN, CFA
CHIEF INVESTMENT OFFICER, PORTFOLIO MANAGER
ANALYTIC INVESTORS, LLC ("ANALYTIC")
As Chief Investment Officer, Dennis Bein oversees the implementation of Analytic's investment strategies. He is a major contributor to Analytic's ongoing research efforts as well as to the new product development efforts and strategy applications. As Portfolio Manager, Bein directs the Old Mutual/Claymore Long-Short Fund's (the "Fund's") management team on day-to-day portfolio management and research related to the Fund's equity-based investment strategies. Bein joined Analytic in 1995 and has worked as an investment professional since 1990. He is a CFA charter-holder and earned an M.B.A. from the Anderson Graduate School of Management at the University of California, Riverside.

The Fund is managed by Analytic Investors, LLC. In the following interview, Chief Investment Officer and Portfolio Manager Dennis Bein, CFA, explains the factors that impacted the Fund's performance for the fiscal year ended December 31, 2008.

We utilize quantitative models to develop an equity portfolio that we believe offers the potential for capital appreciation over time. The portfolio is constructed with a level of diversification and risk similar to that of the S&P 500, but is designed with the objective of outperforming the index over a full market cycle by having its long positions invested in the stocks that we believe will outperform, while selling short the stocks that we believe will underperform. (1) To generate income and help reduce volatility, we then apply a call option overlay. Finally, to potentially enhance returns, we also engage in asset allocation strategies by purchasing or selling futures contracts on U.S. or foreign securities indices as well as foreign currency forward contracts and other assets.

STOCK SELECTION. We begin by analyzing stock characteristics rather than focusing on individual stocks as many investment managers do. Our quantitative review is based on sophisticated mathematical models focused on variables that cover multiple dimensions of a stock's value, such as its valuation, growth potential, historical return patterns, liquidity and risk. The models identify characteristics that investors are currently rewarding or punishing by examining a universe of approximately 3,000 stocks to determine which financial characteristics are shared by the market's largest gaining or losing stocks. Stocks possessing favorable characteristics are ranked and become candidates for the long portfolio. Stocks that possess unfavorable characteristics are candidates for the short portfolio. Ultimately a portfolio of at least 75 highly-ranked stocks is combined with short positions of at least 20 low-ranked stocks. We monitor the portfolio on a real-time basis utilizing our proprietary management system, which identifies media events or changes in fundamental factors that are potentially significant for the portfolio holdings. However, we trade securities only when we believe the incremental return potential will exceed the associated transaction costs.

OPTIONS OVERLAY. Our process is unique because we typically do not write (sell) call options on individual securities held in the Fund's portfolio as a traditional covered call fund might. We prefer to sell call options on indices because we have strong convictions about the stocks held in the Fund's portfolio. This strategy helps preserve the upside potential of the Fund's individual equity holdings, which is more important to us than giving away the upside potential of the market sectors on which we have written the calls. We believe giving away market or sector upside potential in exchange for lower overall volatility and a higher yield provided by the call option premiums benefits the Fund.

ASSET ALLOCATION. We also engage in asset allocation strategies for the Fund by purchasing or selling futures contracts on U.S. or foreign securities indices, foreign currencies and other assets. This enables us to attempt to enhance Fund returns, to hedge against market and other risks in the portfolio and to obtain market exposure with reduced transaction costs. Essentially we take long and short equity markets and currency futures positions based on our global research models.

WHAT IS A SHORT SALE?
A short sale is three-step trading strategy that seeks to capitalize on an anticipated decline in the price of a security. First, arrangements are made to borrow shares of the security, typically from a broker. Next, the investor will sell the borrowed shares immediately in the open market with the intention of buying them back at some point in the future. Finally, to complete the cycle, at a later date the investor will repurchase the shares (hopefully at a lower price) and will return them to the lender. In the end, the investor will receive the difference if the share price falls, but will of course incur a loss if it rises.

(1) The S&P 500 is an unmanaged, capitalization-weighted index of 500 stocks that cover approximately 75% of the U.S. equity market. It is a widely used gauge of the overall performance of the U.S. equity market.

Annual Report | December 31, 2008 | 5

OLA | Old Mutual/Claymore Long-Short Fund | QUESTIONS & ANSWERS continued

WHAT IS AN INDEX OPTION?
An index option is a contract which gives the buyer the right to participate in market gains over and above (in the case of a call) or below (in the case of a put) a specified price (the strike price) on or before a predetermined date (the expiration date). After this pre-determined date, the option and its corresponding rights expire. For example, the seller of an index call option is obligated, until the expiration date, to pay the holder of the option the difference between the index price and the option's strike price, upon the holder's request. The price of the option is determined from trading activity in the options market and generally reflects the relationship between the current price for the index and the strike price, as well as the time remaining until the expiration date.

Essentially all equity indices posted negative returns during 2008. The S&P 500, which is generally regarded as a good indicator of the broad stock market, returned -37.00% for the year. All ten sectors within the S&P 500 posted negative returns. The weakest sector was financials, down more than 50%; the strongest was consumer staples with a negative return of 14%.

The market value and NAV of the Fund's shares fluctuate from time to time, and the Fund's market value may be higher or lower than its NAV. The current discount to NAV may provide an opportunity for suitable investors to purchase shares of the Fund below the market value of the securities in the underlying port-folio. We believe that, over the long term, the progress of the NAV will be reflected in the market price return to shareholders.

The Fund provided investors with consistent quarterly distributions of $0.40 per share during 2008. This represents an annualized distribution rate of 20.05% based upon the closing market price of $7.98 on December 31, 2008. Each of the distributions was accompanied by a letter detailing the expected characterization of the distribution for tax purposes. (These letters are also posted on the Fund's website.)

Analytic's process is based on the fundamental belief that there is persistency in the types of stock characteristics investors prefer, and we believe that portfolios that reflect these biases will add value in the long run. Investor behavior observed during the first six months of 2008 was quite consistent with that seen over recent years. Thematically, economic uncertainty ruled the second half of 2008, as investor sentiment swung between optimism and pessimism and the market was highly volatile. In this crisis-like atmosphere, Analytic's investment process was ineffective, hindered primarily by an emphasis on companies with attractive characteristics such as price momentum, as these companies generally performed well throughout the first half of the year but were penalized severely during the second half of the period. Also negative for performance was the Fund's lack of emphasis on high dividend yielding companies, as these companies generally performed poorly in the first half of the year but were rewarded during the last half of the period. Avoiding highly levered companies helped performance, as these companies were penalized over the period. An emphasis on companies with strong relative earnings yield helped during the first half of the period, as these companies' stocks outperformed, but severely hurt performance during the second half of the period as these companies' stocks were penalized by investors.

6 | Annual Report | December 31, 2008

OLA | Old Mutual/Claymore Long-Short Fund | QUESTIONS & ANSWERS continued

A short position in American International Group (AIG) (not held in the portfolio at period end), a world leader in financial and insurance services, also contributed to performance. Investors were overly concerned that the big insurance company was being backed into a corner by its large exposure to mortgages, causing shares to plummet. Shortly after, the Federal Reserve Board decided to allow the Federal Reserve Bank of New York to lend up to $85 billion to the American International Group in a plan aimed at saving the insurer from a "disorderly failure" that could wreak economic havoc.

A notable long position that added value was Electronic Data Systems Corp. (EDS) (not held in the portfolio at period end), a global business and technology services company. Its shares moved up sharply in May when Hewlett-Packard Co. announced that it had reached an agreement to acquire EDS at a significant premium to the prior stock price.

A long position in Corning Inc. (0.4% of total common stocks and securities sold short), a global, technology-based company that operates in display technologies, telecommunications, environmental technologies and life sciences, further hindered Fund performance, as the maker of glass for LCD televisions and computers, warned of disappointing glass sales volume and announced plans to reduce manufacturing capacity and incur restructuring charges.

A further negative was a short position in William Wrigley Jr. Company (not held in the portfolio at period end), the world's leading chewing gum manufacturer. The company's shares rose when the privately owned confectionary giant Mars Inc. announced that it would team up with billionaire Warren Buffet to purchase Wrigley.

The global asset allocation strategy detracted from returns during the period. Most of the negative performance occurred in September, with both the equity and currency components of the strategy posting losses as rising risk aversion, global deleveraging and weakening economic activity hurt factor returns. Almost all equity factors had negative returns over the period, with valuation factors continuing their recent bad run, as markets continue to react more to the changing economic environment than to relative valuation plays. Our long tactical asset allocation equity position was unsuccessful as global equity markets were down sharply over the period.

Within the currency portion of the strategy, positive returns to relative strength and changes in interest rates were offset by large negative returns to interest differentials and valuation.

Analytic intends to continue to emphasize stocks with attractive historical price-to-earnings and cash-flow-to-price ratios. We also intend to focus on select companies with above-average interest coverage, while de-emphasizing companies with higher-than-average financial leverage. We further anticipate continuing to emphasize companies with above-average asset utilization, while moving away from companies with high trading volume and above-average analyst dispersion, which may reflect greater uncertainty about a company's outlook.

We believe that the Fund's structure, with a long and short equity portfolio, an index options program to preserve upside potential of individual securities, and an asset allocation strategy for exposure to world markets has the potential to provide attractive returns in a wide variety of market conditions.

Annual Report | December 31, 2008 | 7

OLA | Old Mutual/Claymore Long-Short Fund | QUESTIONS & ANSWERS continued

As with any stock, the price of the Fund's common shares will fluctuate with market conditions and other factors. Shares of closed-end management investment companies frequently trade at a discount from their net asset value. If you sell your common shares, you may receive more or less than your original investment. The common shares are designed for long-term investors and should not be treated as a vehicle for trading.

The Fund will ordinarily have substantial exposure (both long and short) to common stocks and other equity securities in pursuing its investment objectives and policies. The market price of common stocks and other equity securities in which the Fund invests may go up or down, sometimes rapidly or unpredictably. Equity securities may decline in value due to factors affecting equity securities markets generally, particular industries represented in those markets or the issuer itself.

The Fund makes substantial use of short sales for investment and risk management purposes, including when Analytic anticipates that the market price of securities will decline or will underperform relative to other securities held in the Fund's portfolio. The Fund intends to take short equity positions in an amount equal to approximately 30% of the Fund's net assets at the time of sale, but reserves the flexibility to hold short positions of up 70% of net assets. Short sales are transactions in which the Fund sells a security or other instrument (such as an option, forward, futures or other derivative contract) that it does not own. When the Fund engages in a short sale on a security, it must borrow the security sold short and deliver it to the counterparty. The Fund will ordinarily have to pay a fee or premium to borrow particular securities and be obligated to repay the lender of the security any dividends or interest that accrue on the security during the period of the loan. The amount of any gain from a short sale will be decreased, and the amount of any loss increased, by the amount of the premium, dividends, interest or expenses the Fund pays in connection with the short sale. Short sales expose the Fund to the risk that it will be required to cover its short position at a time when the securities have appreciated in value, thus resulting in a potentially unlimited loss to the Fund.

The distributions shareholders receive from the Fund are based primarily on the dividends it earns from its equity investments as well as the gains the Fund receives from writing options and using other derivative instruments, closing out short sales and selling portfolio securities, each of which can vary widely over the short and long term. The dividend income from the Fund's investments in equity securities will be influenced by both general economic activity and issuer-specific factors. In the event of a recession or adverse events affecting a specific industry or issuer, an issuer of equity securities held by the Fund may reduce the dividends paid on such securities. If prevailing market interest rates decline, interest rates on any debt instruments held by the Fund, and shareholders' income from the Fund, would likely decline as well.

There are various risks associated with the Option Strategy. The purchaser of an index option written by the Fund has the right to any appreciation in the cash value of the index over the strike price on the expiration date. Therefore, as the writer of an index call option; the Fund forgoes the opportunity to profit from increases in the index over the strike price of the option. However, the Fund has retained the risk of loss (net of premiums received) should the price of the Fund's portfolio securities decline. Similarly, as the writer of a call option on an individual security held in the Fund's portfolio, the Fund forgoes, during the option's life, the opportunity to profit from increases in the market value of the security covering the call option above the sum of the premium and the strike price of the call but has retained the risk of loss (net of premiums received) should the price of the underlying security decline. The value of options written by the Fund, which will be priced daily, will be affected by, among other factors, changes in the value of underlying securities (including those comprising an index), changes in the dividend rates of underlying securities, changes in interest rates, changes in the actual or perceived volatility of the stock market and underlying securities and the remaining time to an option's expiration. The value of an option also may be adversely affected if the market for the option is reduced or becomes less liquid.

An investment in the Fund is subject to certain risks and other considerations, including, but not limited to: Equity Risk; Short Sale Risk; Options Risk, Management Risk; Tax Treatment of Distributions; Derivatives Risk; Counterparty Risk; Credit Risk; Income Risk; Medium- and Smaller-Company Risk; Focused Investment Risk; Interest Rate Risk; Liquidity Risk; Market Disruption and Geopolitical Risk; Leverage Risk; Foreign Investment Risk; Other Investment Companies Risk; and Inflation/Deflation Risk.

8 | Annual Report | December 31, 2008

OLA | Old Mutual/Claymore Long-Short Fund

Fund SUMMARY | AS OF DECEMBER 31, 2008 (unaudited)

Share Price $ 7.98
Common Share Net Asset Value $ 10.24
Premium/(Discount) to NAV -22.07%
Net Assets ($000) $ 194,666
--------------------------------------------------------------------------------

TOTAL RETURNS
--------------------------------------------------------------------------------
(INCEPTION 8/25/05) MARKET NAV
--------------------------------------------------------------------------------
One Year -39.88% -35.09%
Three Year - average annual -12.51% -10.05%
Since Inception - average annual -15.71% -8.91%
--------------------------------------------------------------------------------

SECTOR BREAKDOWN %*
--------------------------------------------------------------------------------
Information Technology 14.5%
Financials 14.1%
Consumer Staples 12.7%
Health Care 12.7%
Industrials 12.4%
Consumer Discretionary 12.1%
Energy 9.8%
Telecommunications 4.3%
Materials 4.2%
Utilities 3.2%
--------------------------------------------------------------------------------

* % of common stocks and securities sold short

Securities are classified by sectors that represent broad groupings of related
industries.

TOP TEN % OF NET
LONG-TERM COMMON STOCKS ASSETS
--------------------------------------------------------------------------------
Exxon Mobil Corp. 4.6%
Procter & Gamble Co. 2.9%
AT&T, Inc. 2.6%
Microsoft Corp. 2.5%
Chevron Corp. 2.3%
Hewlett-Packard Co. 2.1%
Verizon Communications, Inc. 2.1%
Wells Fargo & Co. 1.8%
Wal-Mart Stores, Inc. 1.6%
Philip Morris International, Inc. 1.6%
--------------------------------------------------------------------------------

 % OF NET
TOP FIVE SECURITIES SOLD SHORT ASSETS
--------------------------------------------------------------------------------
Pitney Bowes, Inc. 1.2%
Autozone, Inc. 1.0%
Clorox Co. 1.0%
Affiliated Computer Services, Inc. - Class A 0.9%
General Mills, Inc. 0.9%
--------------------------------------------------------------------------------

Past performance does not guarantee future results. All portfolio data is subject to change daily. For more current information, please visit www.claymore.com/ola. The above summaries are provided for informational purposes only and should not be viewed as recommendations.

 [LINE CHART]

 NAV Share Price
 1/2/08 $ 15.45 $ 17.55
 15.65 17.6
 15.56 17.22
 15.49 17.34
 15.33 17.09
 15.26 17.35
 15.51 17.41
 15.35 17.16
 15.45 17.27
 15.19 16.91
 15.01 16.74
 14.58 16.5
 14.37 16.36
 14.1 15.75
 14.15 15.74
 14.22 16.04
 14.36 15.97
 14.59 15.97
 14.67 16.14
 14.9 16.23
 15.22 16.25
 15.28 16.3
 15.14 16.44
 14.81 16.08
 14.53 16
 14.6 15.9
 14.47 15.84
 14.54 15.89
 14.55 16.21
 14.86 16.39
 14.44 16.39
 14.39 16.38
 14.43 16.62
 14.58 16.61
 14.47 16.53
 14.53 16.55
 14.81 16.63
 15 16.66
 15.05 16.68
 14.84 16.58
 14.66 16.28
 14.46 16.3
 14.39 16.16
 14.32 16.43
 14.13 16.12
 14.03 15.99
 13.76 15.81
 14.3 16.22
 13.81 15.76
 13.8 15.67
 13.38 15.4
 13.09 15.12
 13.46 15.64
 12.94 15.35
 13.19 15.5
 13.37 15.54
 13.42 15.71
 13.33 15.66
 13.37 15.6
 13.34 15.64
 13.47 15.68
 13.83 16.06
 13.98 16.04
 13.98 15.96
 14.03 16.03
 13.97 16.15
 13.97 16.12
 13.85 16.07
 13.91 16.18
 13.7 16.04
 13.63 15.96
 13.66 15.96
 13.99 16.02
 13.9 16.1
 14.1 16.28
 14.13 16.27
 14 16.25
 14.04 16.46
 14.19 16.49
 14.32 16.44
 14.26 16.42
 14.19 16.47
 14.23 16.52
 14.52 16.51
 14.51 16.48
 14.41 16.53
 14.45 16.46
 14.24 16.4
 14.41 16.41
 14.35 16.29
 14.49 16.48
 14.48 16.41
 14.54 16.56
 14.67 16.49
 14.75 16.55
 14.75 16.6
 14.64 16.46
 14.42 16.46
 14.47 16.47
 14.4 16.33
 14.47 16.43
 14.56 16.56
 14.69 16.54
 14.78 16.53
 14.67 16.35
 14.65 16.4
 14.66 16.34
 14.74 16.58
 14.39 16.22
 14.43 16.3
 14.42 16.09
 13.83 15.34
 13.66 15.45
 13.81 15.57
 13.76 15.55
 13.65 15.46
 13.64 15.18
 13.64 15.34
 13.49 15.15
 13.4 15.23
 13.28 15.2
 13.34 15.38
 13.19 15.09
 13.1 15.05
6/30/08 13.23 15.19
 13.16 15.05
 12.88 14.87
 12.75 15.03
 12.76 14.99
 12.97 15.07
 12.9 15.02
 12.93 15.08
 12.68 14.83
 12.3 14.88
 12.19 14.72
 12.45 14.77
 12.64 14.83
 12.66 14.89
 12.8 14.93
 12.96 14.71
 12.75 14.55
 12.36 14.51
 12.55 14.82
 12.5 14.76
 12.67 14.78
 12.95 14.87
 12.89 14.77
 12.78 14.65
 12.54 14.64
 12.73 14.76
 12.75 14.67
 12.41 14.76
 12.77 14.68
 12.64 14.58
 12.45 14.68
 12.41 14.8
 12.56 14.82
 12.55 14.67
 12.47 14.51
 12.39 14.53
 12.47 14.68
 12.49 14.79
 12.65 14.85
 12.47 14.72
 12.44 14.64
 12.53 14.75
 12.67 14.9
 12.66 14.8
 12.71 14.7
 12.66 14.5
 12.34 14.23
 12.35 14.13
 12.4 14.31
 12.01 14.12
 12.15 14.21
 11.66 13.89
 11.54 13.94
 10.93 13.58
 10.71 13.61
 10.28 12.99
 10.35 13.28
 10.98 13.72
 10.63 13.53
 10.49 13.28
 10.39 13.11
 10.49 13.36
 10.4 13.31
 9.75 12.36
 10.1 12.83
 10.23 12.86
 10.05 12.42
 10.03 12.51
 9.05 11.92
 8.44 11.45
 7.9 11.28
 7.09 10.6
 6.85 10.48
 8.01 11.63
 8.4 11.45
 7.94 10.52
 8.36 10.78
 8.46 10.76
 9.02 11.22
 8.88 11.12
 8.5 10.75
 8.48 10.97
 8.35 10.82
 8.45 10.67
 9.18 11.29
 9.23 11.04
 9.36 11.12
 9.45 11.33
 9.44 11.35
 9.73 11.52
 9.35 11.15
 8.93 10.82
 9.1 11
 9.02 10.98
 8.75 10.92
 8.38 10.52
 8.48 10.84
 8.27 10.54
 8.15 10.35
 8.01 10.4
 7.29 9.98
 6.43 9.59
 6.6 10
 7.5 9.86
 7.37 9.87
 7.6 10.07
 7.82 10.21
 7.14 9.74
 7.29 9.95
 7.6 10.04
 7.3 9.92
 7.45 10.13
 7.75 10.3
 7.6 10.21
 7.86 10.32
 7.36 9.77
 7.49 9.8
 7.51 9.72
 7.8 10.03
 7.63 10.01
 7.53 9.86
 7.53 9.97
 7.54 9.77
 7.42 9.75
 7.75 9.79
 7.76 9.83
 7.65 9.85
 7.8 10.04
 12/31/08 7.98 10.24

 [BAR CHART]

Mar 08 $ 0.4
Jun 08 0.4
Sep 08 0.4
Dec 08 0.4

 % OF NET
FUND BREAKDOWN ASSETS
--------------------------------------------------------------------------------
Long-Term Investments 124.7%
Short-Term Investments 12.1%
--------------------------------------------------------------------------------
Total Investments 136.8%
Securities Sold Short -38.1%
Total Value of Options Written -2.0%
Other Assets less Liabilities 3.3%
--------------------------------------------------------------------------------
Total Net Assets 100.0%
--------------------------------------------------------------------------------

 Annual Report | December 31, 2008 | 9

OLA | Old Mutual/Claymore Long-Short Fund

Portfolio of INVESTMENTS | DECEMBER 31, 2008

NUMBER
OF SHARES VALUE
-----------------------------------------------------------------------------------------
 LONG-TERM INVESTMENTS - 124.7%
 CONSUMER DISCRETIONARY - 13.9%
 1,951 Amazon.com, Inc. (a) $ 100,047
 29,643 Best Buy Co., Inc. (b) 833,265
 65,677 Big Lots, Inc. (a)(c) 951,660
 3,349 Coach, Inc. (a) 69,559
 143,571 Comcast Corp. - Class A (b) 2,423,478
 19,076 Dillard's, Inc. - Class A 75,732
 7,705 DIRECTV Group, Inc. (a) 176,522
 108,494 Eastman Kodak Co. (b) 713,891
 31,449 Expedia, Inc. (a) 259,140
 51,897 Family Dollar Stores, Inc. (c) 1,352,955
 258,748 Ford Motor Co. (a)(b) 592,533
 176 GameStop Corp. (a) 3,812
 31,085 Gap, Inc. 416,228
 12,152 Genuine Parts Co. 460,075
 88,267 H&R Block, Inc. (b) 2,005,426
 48,511 Harman International Industries, Inc. (b) 811,589
 167,332 Interpublic Group of Companies, Inc. (a)(b) 662,635
 42,217 Johnson Controls, Inc. (b) 766,661
 1,361 Kohl's Corp. (a) 49,268
 329 Lowe's Cos., Inc. 7,080
 3,255 Limited Brands, Inc. 32,680
 28,690 McDonald's Corp. (b) 1,784,231
 30,954 McGraw-Hill Cos., Inc. (b) 717,823
 27,498 New York Times Co. - Class A 201,560
 81,303 Newell Rubbermaid, Inc. (b) 795,143
 204,938 News Corp. - Class A (c) 1,862,886
 35,016 Nike, Inc. - Class B (b) 1,785,816
 68,875 Office Depot, Inc. (a) 205,248
 24,964 Polo Ralph Lauren Corp. (c) 1,133,615
 15,637 RadioShack Corp. 186,706
 52,232 Snap-On, Inc. (c) 2,056,896
 373 Staples, Inc. 6,684
 188 Tiffany & Co. 4,442
 163,009 Time Warner, Inc. (c) 1,639,871
 106 TJX Cos., Inc. 2,180
 35,309 Walt Disney Co. (b) 801,161
 53,916 Wendy's/Arby's Group, Inc. - Class A 266,345
 64,052 Wyndham Worldwide Corp. 419,541
 11,456 Yum! Brands, Inc. 360,864
-----------------------------------------------------------------------------------------
 26,995,248
-----------------------------------------------------------------------------------------

NUMBER
OF SHARES VALUE
-----------------------------------------------------------------------------------------
 CONSUMER STAPLES - 16.9%
 43,979 Altria Group, Inc. (b) $ 662,324
 41,574 Archer-Daniels-Midland Co. (c) 1,198,578
 4,666 Avon Products, Inc. 112,124
 32,163 Brown-Forman Corp. - Class B (c) 1,656,073
 21,270 Coca-Cola Co. (b) 962,893
 2,541 Colgate-Palmolive Co. 174,160
 43,939 Costco Wholesale Corp. (c) 2,306,798
 26,629 CVS/Caremark Corp. (b) 765,317
 69,203 Dean Foods Co. (a)(b) 1,243,578
 53,525 Estee Lauder Cos., Inc. - Class A (b) 1,657,134
 17,597 Kraft Foods, Inc. 472,479
 26,695 Molson Coors Brewing Co. - Class B (c) 1,305,919
 32,897 PepsiCo, Inc. (b) 1,801,769
 72,715 Philip Morris International, Inc. (b) 3,163,830
 90,690 Procter & Gamble Co. (b) 5,606,456
 84,152 Sara Lee Corp. (b) 823,848
 35,880 SUPERVALU, Inc. 523,848
 112,549 SYSCO Corp. (b) 2,581,874
 130,198 Tyson Foods, Inc. - Class A (b) 1,140,534
 756 UST, Inc. 52,451
 59,148 Walgreen Co. (b) 1,459,181
 57,028 Wal-Mart Stores, Inc. (b) 3,196,990
-----------------------------------------------------------------------------------------
 32,868,158
-----------------------------------------------------------------------------------------
 ENERGY - 13.8%
 15,377 Baker Hughes, Inc. (b) 493,140
 15,240 Cabot Oil & Gas Corp. 396,240
 61,223 Chevron Corp. (b) 4,528,665
 29,561 ConocoPhillips (c) 1,531,260
 6,836 Devon Energy Corp. (b) 449,194
 104,195 El Paso Corp. (b) 815,847
 6,006 EOG Resources, Inc. 399,880
 111,278 Exxon Mobil Corp. (b) 8,883,323
 65,433 Halliburton Co. (b) 1,189,572
 5,966 Hess Corp. 320,016
 1,041 Marathon Oil Corp. 28,482
 1,411 Massey Energy Co. 19,458
 19,041 Murphy Oil Corp. (b) 844,468
 6,957 National Oilwell Varco, Inc. (a) 170,029
 7,491 Noble Corp. (Cayman Islands) 165,476
 12,578 Noble Energy, Inc. (b) 619,089
 35,136 Occidental Petroleum Corp. (c) 2,107,809

See notes to financial statements.

10 | Annual Report | December 31, 2008

OLA | Old Mutual/Claymore Long-Short Fund | PORTFOLIO OF INVESTMENTS continued

NUMBER
OF SHARES VALUE
-----------------------------------------------------------------------------------------
 ENERGY (CONTINUED)
 6,732 Peabody Energy Corp. $ 153,153
 35,978 Pioneer Natural Resources Co. (b) 582,124
 53,736 Schlumberger Ltd. (Netherlands Antilles) (b) 2,274,645
 3,418 Sunoco, Inc. 148,546
 3,421 Valero Energy Corp. 74,030
 41,204 Williams Cos., Inc. (b) 596,634
 1,264 XTO Energy, Inc. 44,581
-----------------------------------------------------------------------------------------
 26,835,661
-----------------------------------------------------------------------------------------
 FINANCIALS - 17.3%
 14,990 American Express Co. 278,065
 9,956 AON Corp. 454,790
 115 Apartment Investment & Management Co.- Class A - REIT 1,328
 20,304 AvalonBay Communities, Inc. - REIT (c) 1,230,016
 77,982 Bank of America Corp. (c) 1,097,987
 63,363 Bank of New York Mellon Corp. (c) 1,795,074
 10,089 BB&T Corp. 277,044
 22,771 Boston Properties, Inc. - REIT (c) 1,252,405
 13,630 CB Richard Ellis Group, Inc. - Class A (a) 58,882
 109,207 Charles Schwab Corp. (c) 1,765,877
 35,219 Chubb Corp. (b) 1,796,169
 12,354 Citigroup, Inc. 82,895
 1,226 CME Group, Inc. 255,143
 941 Developers Diversified Realty Corp. - REIT 4,592
 28,948 Discover Financial Services 275,874
 20,836 Federated Investors, Inc. - Class B 353,379
 13,244 Fifth Third Bancorp 109,395
 69,422 Host Hotels & Resorts, Inc. - REIT (b) 525,525
 132,483 Hudson City Bancorp, Inc. (b) 2,114,429
 96,479 Janus Capital Group, Inc. (b) 774,726
 39,185 JPMorgan Chase & Co. (c) 1,235,503
 36,445 Kimco Realty Corp.- REIT (b) 666,215
 27,261 Leucadia National Corp. (b) 539,768
 50,105 Loews Corp. (c) 1,415,466
 24,943 Marsh & McLennan Cos., Inc. (c) 605,367
 19,727 Merrill Lynch & Co., Inc. (d) 229,622
 25,095 Northern Trust Corp. (c) 1,308,453
 52,313 NYSE Euronext (c) 1,432,330
 10,042 Plum Creek Timber Co., Inc. - REIT 348,859
 7,400 PNC Financial Services Group, Inc. 362,600
 9,010 Principal Financial Group, Inc. 203,356
 55,084 Progressive Corp. (b) 815,794
 804 Prologis - REIT 11,168
 8,545 Public Storage - REIT (b) 679,327

NUMBER
OF SHARES VALUE
-----------------------------------------------------------------------------------------
 FINANCIALS (CONTINUED)
 68,613 Regions Financial Corp. (b) $ 546,159
 645 SunTrust Banks, Inc. 19,053
 33,746 T Rowe Price Group, Inc. (c) 1,195,958
 12,877 Torchmark Corp. 575,602
 49,673 Travelers Cos., Inc. (b) 2,245,220
 46,307 US Bancorp. (b) 1,158,138
 15,033 Wachovia Corp. 83,283
 119,671 Wells Fargo & Co. (b) 3,527,901
-----------------------------------------------------------------------------------------
 33,708,737
-----------------------------------------------------------------------------------------
 HEALTH CARE - 17.7%
 18,641 Abbott Laboratories (b) 994,870
 59,988 Aetna, Inc. (c) 1,709,658
 4,081 Allergan, Inc. 164,546
 62,189 AmerisourceBergen Corp. (c) 2,217,660
 33,135 Amgen, Inc. (a)(b) 1,913,546
 21,042 Baxter International, Inc. (c) 1,127,641
 8,376 Becton Dickinson & Co. (b) 572,835
 61,042 Bristol-Myers Squibb Co. (c) 1,419,226
 70,356 Cardinal Health, Inc. (b) 2,425,171
 43,018 Cigna Corp. (b) 724,853
 44,611 Dentsply International, Inc. (b) 1,259,815
 3,525 Express Scripts, Inc. (a) 193,805
 6,935 Genzyme Corp. (a)(b) 460,276
 7,643 Gilead Sciences, Inc. (a) 390,863
 36,016 Humana, Inc. (a)(c) 1,342,676
 41,942 Johnson & Johnson (c) 2,509,390
 45,795 Life Technologies Corp. (a)(c) 1,067,481
 58,781 McKesson Corp. (c) 2,276,588
 56,664 Medco Health Solutions, Inc. (a)(c) 2,374,788
 12,489 Medtronic, Inc. 392,404
 54,733 Merck & Co, Inc. (b) 1,663,883
 74,527 PerkinElmer, Inc. (c) 1,036,671
 124,604 Pfizer, Inc. (b) 2,206,737
 45,585 Stryker Corp. (c) 1,821,121
 258,448 Tenet Healthcare Corp. (a) 297,215
 4,130 Thermo Fisher Scientific, Inc. (a) 140,709
 12,947 UnitedHealth Group, Inc. (b) 344,390
 938 Varian Medical Systems, Inc. (a) 32,868
 9,781 Watson Pharmaceuticals, Inc. (a) 259,881
 5,801 Wyeth 217,596
 24,756 Zimmer Holdings, Inc. (a)(b) 1,000,638
-----------------------------------------------------------------------------------------
 34,559,801
-----------------------------------------------------------------------------------------

See notes to financial statements.

Annual Report | December 31, 2008 | 11

OLA | Old Mutual/Claymore Long-Short Fund | PORTFOLIO OF INVESTMENTS continued

NUMBER
OF SHARES VALUE
-----------------------------------------------------------------------------------------
 INDUSTRIALS - 12.3%
 47,734 Boeing Co. (b) $ 2,036,810
 10,340 C.H. Robinson Worldwide, Inc. (b) 569,010
 41,287 CSX Corp. (c) 1,340,589
 26,761 Cummins, Inc. (b) 715,322
 159 Fastenal Co. 5,541
 29,640 FedEx Corp. (b) 1,901,406
 29,861 Fluor Corp. (c) 1,339,863
 28,912 General Dynamics Corp. (c) 1,665,042
 93,695 General Electric Co. (c) 1,517,859
 21,931 Jacobs Engineering Group, Inc. (a)(c) 1,054,881
 25,838 Lockheed Martin Corp. (c) 2,172,459
 19,232 Manitowoc Co., Inc. 166,549
 9,435 Norfolk Southern Corp. 443,917
 3,951 Northrop Grumman Corp. 177,953
 13,560 Pall Corp. 385,511
 8,940 Parker Hannifin Corp. (b) 380,308
 18,731 Precision Castparts Corp. (b) 1,114,120
 36,558 Raytheon Co. (b) 1,865,920
 19,336 Republic Services, Inc. 479,339
 41,524 RR Donnelley & Sons Co. 563,896
 6,595 Tyco International Ltd. (Bermuda) (b) 142,452
 37,948 Union Pacific Corp. (b) 1,813,914
 23,428 Waste Management, Inc. (b) 776,404
 16,219 WW Grainger, Inc. (c) 1,278,706
-----------------------------------------------------------------------------------------
 23,907,771
-----------------------------------------------------------------------------------------
 INFORMATION TECHNOLOGY - 18.4%
 66,560 Analog Devices, Inc. (b) 1,265,971
 9,985 Apple, Inc. (a)(b) 852,220
 16,175 Applied Materials, Inc. 163,853
 694 Autodesk, Inc. (a) 13,637
 9,615 Automatic Data Processing, Inc. 378,254
 618 Broadcom Corp. - Class A (a) 10,487
 75,295 CA, Inc. (c) 1,395,216
 92,130 Cisco Systems, Inc. (a)(b) 1,501,719
 49,625 Computer Sciences Corp. (a)(b) 1,743,823
 9,016 Compuware Corp. (a) 60,858
 80,795 Convergys Corp. (a)(b) 517,896
 123,817 Corning, Inc. (c) 1,179,976
 107,799 Dell, Inc. (a)(c) 1,103,862
 60,587 eBay, Inc. (a)(b) 845,795
 32,301 Electronic Arts, Inc. (a)(b) 518,108
 57,943 EMC Corp. (a)(b) 606,663
 2,985 Google, Inc. - Class A (a)(c) 918,335

NUMBER
OF SHARES VALUE
-----------------------------------------------------------------------------------------
 INFORMATION TECHNOLOGY (CONTINUED)
 114,739 Hewlett-Packard Co. (b) $ 4,163,878
 200,521 Intel Corp. (b) 2,939,638
 10,241 International Business Machines Corp. (b) 861,883
 40,617 Jabil Circuit, Inc. 274,165
 5,813 Kla-Tencor Corp. 126,665
 36,410 Lexmark International, Inc. - Class A (a)(b) 979,429
 31,951 MEMC Electronic Materials, Inc. (a)(b) 456,260
 4,055 Microchip Technology, Inc. 79,194
 250,081 Microsoft Corp. (b) 4,861,575
 101,506 Molex, Inc. (b) 1,470,822
 123,494 Motorola, Inc. (b) 547,078
 22,081 NetApp, Inc. (a) 308,472
 31,261 QLogic Corp. (a) 420,148
 4,261 QUALCOMM, Inc. 152,672
 16,622 Salesforce.com, Inc. (a)(b) 532,070
 65,865 Sun Microsystems, Inc. (a)(b) 251,604
 5,032 Teradata Corp. (a) 74,625
 3,651 Teradyne, Inc. (a) 15,407
 141,718 Texas Instruments, Inc. (b) 2,199,463
 20,107 Tyco Electronics Ltd. (Bermuda) 325,934
 259,103 Unisys Corp. (a) 220,238
 49,365 Western Union Co. (b) 707,894
 57,620 Yahoo!, Inc. (a)(b) 702,964
-----------------------------------------------------------------------------------------
 35,748,751
-----------------------------------------------------------------------------------------
 MATERIALS - 4.9%
 35,082 AK Steel Holding Corp. 326,964
 103,216 Alcoa, Inc. (b) 1,162,212
 3,559 Ashland, Inc. 37,405
 9,484 Ball Corp. 394,440
 8,671 CF Industries Holdings, Inc. 426,266
 19,748 Dow Chemical Co. 297,997
 84,836 Du Pont (E.I.) de Nemours & Co. (b) 2,146,351
 48,891 Ecolab, Inc. (c) 1,718,519
 38,333 MeadWestvaco Corp. 428,946
 3,886 Monsanto Co. 273,380
 18,618 Newmont Mining Corp. (b) 757,753
 11,216 Praxair, Inc. 665,782
 240 Rohm & Haas Co. 14,830
 44,960 Sealed Air Corp. (b) 671,702
 4,370 Titanium Metals Corp. 38,500
 3,364 Vulcan Materials Co. 234,067
-----------------------------------------------------------------------------------------
 9,595,114
-----------------------------------------------------------------------------------------

See notes to financial statements.

12 | Annual Report | December 31, 2008

OLA | Old Mutual/Claymore Long-Short Fund | PORTFOLIO OF INVESTMENTS continued

NUMBER
OF SHARES VALUE
-----------------------------------------------------------------------------------------
 TELECOMMUNICATIONS - 5.5%
 32,350 American Tower Corp. - Class A (a)(b) $ 948,502
 179,756 AT&T, Inc. (b) 5,123,046
 169,355 Qwest Communications International, Inc. (b) 616,452
 120,217 Verizon Communications, Inc. (b) 4,075,356
-----------------------------------------------------------------------------------------
 10,763,356
-----------------------------------------------------------------------------------------
 UTILITIES - 4.0%
 35,453 AES Corp. (a) 292,133
 11,561 Allegheny Energy, Inc. 391,455
 3,882 Duke Energy Corp. (b) 58,269
 42,417 Edison International (c) 1,362,434
 7,525 Exelon Corp. 418,465
 11,632 FirstEnergy Corp. 565,083
 9,361 Integrys Energy Group, Inc. 402,336
 70,435 PG&E Corp. (b) 2,726,539
 8,221 Pinnacle West Capital Corp. 264,141
 832 Public Service Enterprise Group, Inc. 24,269
 66,106 TECO Energy, Inc. (b) 816,409
 22,033 Xcel Energy, Inc. 408,712
-----------------------------------------------------------------------------------------
 7,730,245
-----------------------------------------------------------------------------------------
 TOTAL LONG-TERM INVESTMENTS - 124.7%
 (Cost $341,925,484) 242,712,842
-----------------------------------------------------------------------------------------

PRINCIPAL
AMOUNT VALUE
-----------------------------------------------------------------------------------------
 U.S. GOVERNMENT SECURITIES - 11.6%
$ 22,550,000 U.S. Treasury Bill yielding 0.64%
 10/22/09 maturity (c)(e)
 (Cost $22,432,432) 22,488,889
-----------------------------------------------------------------------------------------

NUMBER
OF SHARES VALUE
-----------------------------------------------------------------------------------------
 MONEY MARKET FUNDS - 0.5%
 1,053,531 Dreyfus Institutional Reserve Money Market Fund
 (Cost $1,053,531) 1,053,531
-----------------------------------------------------------------------------------------
 TOTAL SHORT-TERM INVESTMENTS - 12.1%
 (Cost $23,485,963) 23,542,420
-----------------------------------------------------------------------------------------
 TOTAL INVESTMENTS - 136.8%
 (Cost $365,411,447) 266,255,262
 Securities Sold Short - (38.1%)
 (Proceeds $87,853,121) (74,231,399)
 Total Value of Options Written (Premiums received
 $5,563,001)-(2.0%) (3,829,800)
 Other Assets in excess of Other Liabilities - 3.3% 6,472,105
-----------------------------------------------------------------------------------------
 NET ASSETS - 100.0% $ 194,666,168
-----------------------------------------------------------------------------------------

NUMBER
OF SHARES VALUE
-----------------------------------------------------------------------------------------
 SECURITIES SOLD SHORT - 38.1%
 COMMON STOCKS - 38.1%
 CONSUMER DISCRETIONARY - 5.7%
 45,727 Abercrombie & Fitch Co.- Class A $ 1,054,922
 7,065 Apollo Group, Inc. - Class A 541,320
 13,455 Autozone, Inc. 1,876,569
 8,176 Bed Bath & Beyond, Inc. 207,834
 19,414 Black & Decker Corp. 811,699
 2,387 Carnival Corp. (Panama) 58,052
 66,580 CBS Corp. - Class B 545,290
 1,299 Darden Restaurants, Inc. 36,606
 50,686 DR Horton, Inc. 358,350
 678 EW Scripps Co. - Class A 1,498
 61,482 Gannett Co., Inc. 491,856
 30,314 Goodyear Tire & Rubber Co. 180,975
 10,690 Harley-Davidson, Inc. 181,409
 37,416 Home Depot, Inc. 861,316
 21,264 International Game Technology 252,829
 7,834 JC Penney Co., Inc. 154,330
 36,994 KB Home 503,858
 14,537 Macy's, Inc. 150,458
 5,350 Marriott International, Inc. - Class A 104,058
 5,047 Meredith Corp. 86,405
 8,423 Omnicom Group, Inc. 226,747
 12,241 Pulte Homes, Inc. 133,794
 56,039 Scripps Networks Interactive, Inc. - Class A 1,232,858
 2,237 Sherwin-Williams Co. 133,661
 16,836 Stanley Works 574,108
 3,519 Starwood Hotels & Resorts Worldwide, Inc. 62,990
 2,806 Target Corp. 96,891
 2,259 Viacom, Inc. - Class B 43,057
 645 Washington Post Co. - Class B 251,711
-----------------------------------------------------------------------------------------
 11,215,451
-----------------------------------------------------------------------------------------
 CONSUMER STAPLES - 3.8%
 33,506 Clorox Co. 1,861,593
 20,049 Constellation Brands, Inc. - Class A 316,173
 28,149 General Mills, Inc. 1,710,052
 14,285 Hershey Co. 496,261
 21,540 HJ Heinz Co. 809,904
 18,646 Kellogg Co. 817,627
 6,521 Kimberly-Clark Corp. 343,917

See notes to financial statements.

Annual Report | December 31, 2008 | 13

OLA | Old Mutual/Claymore Long-Short Fund | PORTFOLIO OF INVESTMENTS continued

NUMBER
OF SHARES VALUE
-----------------------------------------------------------------------------------------
 CONSUMER STAPLES (CONTINUED)
 4,920 Kroger Co. $ 129,937
 7,368 Lorillard, Inc. 415,187
 11,967 Reynolds American, Inc. 482,390
-----------------------------------------------------------------------------------------
 7,383,041
-----------------------------------------------------------------------------------------
 ENERGY - 2.2%
 30,073 Anadarko Petroleum Corp. 1,159,314
 12,463 Apache Corp. 928,867
 4,702 Chesapeake Energy Corp. 76,031
 1,917 ENSCO International, Inc. 54,424
 26,427 Range Resources Corp. 908,825
 22,017 Tesoro Corp. 289,964
 17,317 Transocean, Inc. (Cayman Islands) 818,228
-----------------------------------------------------------------------------------------
 4,235,653
-----------------------------------------------------------------------------------------
 FINANCIALS - 5.6%
 770 Aflac, Inc. 35,297
 40,958 Allstate Corp. 1,341,784
 20,328 Capital One Financial Corp. 648,260
 47,306 CIT Group, Inc. 214,769
 8,465 Comerica, Inc. 168,030
 9,309 Equity Residential - REIT 277,595
 53,344 First Horizon National Corp. 563,842
 8,974 Goldman Sachs Group, Inc. 757,316
 46,067 Hartford Financial Services Group, Inc. 756,420
 31,612 HCP, Inc. - REIT 877,865
 46,302 Keycorp 394,493
 14,321 Legg Mason, Inc. 313,773
 725 M&T Bank Corp. 41,622
 44,464 Marshall & Ilsley Corp. 606,489
 18,567 MGIC Investment Corp. 64,613
 48,947 Morgan Stanley 785,110
 6,471 Prudential Financial, Inc. 195,813
 16,685 Simon Property Group, Inc. - REIT 886,474
 76,608 SLM Corp. 681,811
 19,751 Vornado Realty Trust - REIT 1,191,973
 54,716 XL Capital Ltd. - Class A (Cayman Islands) 202,449
-----------------------------------------------------------------------------------------
 11,005,798
-----------------------------------------------------------------------------------------
 HEALTH CARE - 2.9%
 17,371 DaVita, Inc. 861,081
 12,743 Eli Lilly & Co. 513,161
 4,680 Intuitive Surgical, Inc. 594,313
 8,862 King Pharmaceuticals, Inc. 94,114
 10,795 Laboratory Corp of America Holdings 695,306
 20,870 Quest Diagnostics, Inc. 1,083,362

NUMBER
OF SHARES VALUE
-----------------------------------------------------------------------------------------
 HEALTH CARE (CONTINUED)
 14,078 St. Jude Medical, Inc. $ 464,011
 37,093 Waters Corp. 1,359,458
-----------------------------------------------------------------------------------------
 5,664,806
-----------------------------------------------------------------------------------------
 INDUSTRIALS - 7.9%
 26,425 3M Co. 1,520,495
 9,807 Burlington Northern Santa Fe Corp. 742,488
 4,395 Caterpillar, Inc. 196,325
 24,501 Danaher Corp. 1,387,002
 15,420 Deere & Co. 590,894
 5,619 Dun & Bradstreet Corp. 433,787
 17,269 Eaton Corp. 858,442
 20,910 Emerson Electric Co. 765,515
 3,924 Expeditors International of Washington, Inc. 130,551
 6,295 Honeywell International, Inc. 206,665
 29,675 Illinois Tool Works, Inc. 1,040,109
 18,790 L-3 Communications Holdings, Inc. 1,386,326
 15,849 PACCAR, Inc. 453,281
 95,405 Pitney Bowes, Inc. 2,430,919
 3,666 Rockwell Automation, Inc. 118,192
 509 Ryder System, Inc. 19,739
 112,055 Southwest Airlines Co. 965,914
 16,307 Textron, Inc. 226,178
 15,567 United Parcel Service, Inc. - Class B 858,676
 20,933 United Technologies Corp. 1,122,009
-----------------------------------------------------------------------------------------
 15,453,507
-----------------------------------------------------------------------------------------
 INFORMATION TECHNOLOGY - 5.2%
 39,729 Affiliated Computer Services, Inc. - Class A 1,825,548
 1,824 Akamai Technologies, Inc. 27,524
 45,714 Altera Corp. 763,881
 107,780 Ciena Corp. 722,126
 8,696 Citrix Systems, Inc. 204,965
 41,263 Fiserv, Inc. 1,500,735
 17,398 Intuit, Inc. 413,898
 58,453 JDS Uniphase Corp. 213,353
 49,060 Linear Technology Corp. 1,085,207
 2,189 Mastercard, Inc. - Class A 312,874
 11,786 National Semiconductor Corp. 118,685
 29,533 Novell, Inc. 114,883
 44,902 Novellus Systems, Inc. 554,091
 55,056 Nvidia Corp. 444,302
 31,625 Oracle Corp. 560,711
 16,687 Paychex, Inc. 438,534
 2,864 Tellabs, Inc. 11,800

See notes to financial statements.

14 | Annual Report | December 31, 2008

OLA | Old Mutual/Claymore Long-Short Fund | PORTFOLIO OF INVESTMENTS continued

NUMBER
OF SHARES VALUE
-----------------------------------------------------------------------------------------
 INFORMATION TECHNOLOGY (CONTINUED)
 3,308 VeriSign, Inc. $ 63,117
 39,327 Xilinx, Inc. 700,807
-----------------------------------------------------------------------------------------
 10,077,041
-----------------------------------------------------------------------------------------
 MATERIALS - 2.0%
 3,556 Allegheny Technologies, Inc. 90,785
 46,175 Bemis Co., Inc. 1,093,424
 7,003 Freeport-McMoRan Copper & Gold, Inc. 171,153
 23,371 International Paper Co. 275,778
 20,719 Nucor Corp. 957,218
 6,402 PPG Industries, Inc. 271,637
 1,696 United States Steel Corp. 63,091
 29,887 Weyerhaeuser Co. 914,841
-----------------------------------------------------------------------------------------
 3,837,927
-----------------------------------------------------------------------------------------
 TELECOMMUNICATIONS - 1.5%
 29,519 CenturyTel, Inc. 806,754
 154,001 Frontier Communications Corp. 1,345,969
 78,426 Windstream Corp. 721,519
-----------------------------------------------------------------------------------------
 2,874,242
-----------------------------------------------------------------------------------------
 UTILITIES - 1.3%
 17,554 Consolidated Edison, Inc. 683,377
 18,496 Dominion Resources, Inc. 662,897
 85,304 Dynegy, Inc. 170,608
 11,633 Entergy Corp. 967,051
-----------------------------------------------------------------------------------------
 2,483,933
-----------------------------------------------------------------------------------------
 TOTAL SECURITIES SOLD SHORT - 38.1%
 (Proceeds $87,853,121) $ 74,231,399
=========================================================================================

CONTRACTS
(100 SHARES EXPIRATION EXERCISE MARKET
PER CONTRACT) OPTIONS WRITTEN(A) DATE PRICE VALUE
---------------------------------------------------------------------------------------------
 CALL OPTIONS WRITTEN (A)
 230 ISE U.S. Reg Banks Index January 2009 $ 22.50 $ 29,900
 108 ISE SIndex January 2009 72.50 11,880
 2,322 KBW Bank Index January 2009 45.00 417,960
 249 Philadelphia Utility Index January 2009 400.00 231,570
 415 S&P 500 Index January 2009 875.00 1,572,850
 240 S&P 500 Index January 2009 925.00 298,800
 1,173 S&P 500 Index January 2009 930.00 1,266,840
---------------------------------------------------------------------------------------------
 TOTAL OPTIONS WRITTEN
 (Premiums received $5,563,001) $ 3,829,800
=============================================================================================

REIT - Real Estate Investment Trust

(a) Non-income producing security.

(b) All or a portion of these securities are held as collateral for Securities Sold Short.

(c) All or a portion of these securities are held as collateral for futures or options.

(d) Effective January 1, 2009, Bank of America completed its acquistion of Merrill Lynch.

(e) Held as collateral for forward exchange currency contracts.

Securities are classified by sectors that represent broad groupings of related industries.

See notes to financial statements.

15 | Annual Report | December 31, 2008

OLA | Old Mutual/Claymore Long-Short Fund

Statement of ASSETS AND LIABILITIES | DECEMBER 31, 2008

ASSETS
 Investments, at value (cost $365,411,447) $ 266,255,262
 Cash 4,872,707
 Unrealized appreciation on forward currency exchange contracts 3,337,081
 Variation margin on futures 196,694
 Dividends and interest receivable 464,877
 Other assets 4,559
-----------------------------------------------------------------------------------------------------------------------------
 Total assets 275,131,180
-----------------------------------------------------------------------------------------------------------------------------

LIABILITIES
 Securities sold short, at value (proceeds $87,853,121) 74,231,399
 Options written, at value (premiums received of $5,563,001) 3,829,800
 Unrealized depreciation on forward currency exchange contracts 2,115,799
 Advisory fee payable 159,646
 Administration fee payable 4,390
 Accrued expenses 123,978
-----------------------------------------------------------------------------------------------------------------------------
 Total liabilities 80,465,012
-----------------------------------------------------------------------------------------------------------------------------

NET ASSETS $ 194,666,168
=============================================================================================================================

COMPOSITION OF NET ASSETS
Common stock, $.01 par value per share; unlimited number of shares
 authorized, 19,005,240 shares issued and outstanding $ 190,052
Additional paid-in capital 320,244,358
Net unrealized depreciation on investments, futures, options, securities sold
 short, forwards and currency translation (80,655,265)
Accumulated net realized loss on investments, futures, options, securities sold
 short, forwards and currency transactions (42,271,894)
Accumulated net investment loss (2,841,083)
-----------------------------------------------------------------------------------------------------------------------------

NET ASSETS $ 194,666,168
=============================================================================================================================
NET ASSET VALUE (BASED ON 19,005,240 COMMON SHARES OUTSTANDING) $ 10.24
=============================================================================================================================

See notes to financial statements.

16 | Annual Report | December 31, 2008

OLA | Old Mutual/Claymore Long-Short Fund

Statement of OPERATIONS | FOR THE YEAR ENDED DECEMBER 31, 2008

INVESTMENT INCOME
 Dividends $ 6,435,561
 Interest 690,783
-----------------------------------------------------------------------------------------------------------------------------
 Total income $ 7,126,344
-----------------------------------------------------------------------------------------------------------------------------

EXPENSES
 Advisory fee 2,729,252
 Dividends on securities sold short 2,329,922
 Custodian fee 499,563
 Trustees'fees and expenses 146,116
 Professional fees 140,911
 Fund accounting 93,807
 Printing expense 77,199
 Administration fee 69,482
 NYSE listing fee 21,228
 Transfer agent fee 18,589
 Insurance 18,361
 Miscellaneous 12,896
-----------------------------------------------------------------------------------------------------------------------------
 Total expenses 6,157,326
-----------------------------------------------------------------------------------------------------------------------------
 NET INVESTMENT INCOME 969,018
-----------------------------------------------------------------------------------------------------------------------------

REALIZED AND UNREALIZED GAIN (LOSS):
 Net realized gain (loss) on:
 Investments $ (66,155,320)
 Futures (23,830,976)
 Options 20,600,660
 Securities sold short 28,088,430
 Foreign currency forwards and currency transactions (13,238,546)
 Net change in unrealized appreciation (depreciation) on:
 Investments (73,627,854)
 Futures 1,048,685
 Options 844,338
 Securities sold short 8,393,619
 Foreign currency forwards and currency translation 3,910,295
-----------------------------------------------------------------------------------------------------------------------------
 NET REALIZED AND UNREALIZED LOSS (113,966,669)
-----------------------------------------------------------------------------------------------------------------------------

NET DECREASE IN NET ASSETS RESULTING FROM OPERATIONS $ (112,997,651)
=============================================================================================================================

See notes to financial statements.

Annual Report | December 31, 2008 | 17

OLA | Old Mutual/Claymore Long-Short Fund

Statement of CHANGES IN NET ASSETS |

 FOR THE FOR THE
 YEAR ENDED YEAR ENDED
 DECEMBER 31, 2008 DECEMBER 31, 2007
-----------------------------------------------------------------------------------------------------------------------------
INCREASE (DECREASE) IN NET ASSETS FROM OPERATIONS
 Net investment income (loss) $ 969,018 $ (1,954,648)
 Net realized gain (loss) on investments, futures, options, securities
 sold short, forwards and currency transactions (54,535,752) 36,920,981
 Net unrealized appreciation (depreciation) on investments, futures,
 options, securities sold short, forwards and currency translation (59,430,917) (25,521,665)
-----------------------------------------------------------------------------------------------------------------------------
 Net increase/(decrease) in net assets resulting from operations (112,997,651) 9,444,668
-----------------------------------------------------------------------------------------------------------------------------

DISTRIBUTIONS TO COMMON SHAREHOLDERS
 From and in excess of net investment income (2,755,313) (30,408,384)
 Return of capital (27,653,071) -
-----------------------------------------------------------------------------------------------------------------------------
 Total distributions to common shareholders (30,408,384) (30,408,384)
-----------------------------------------------------------------------------------------------------------------------------
 Total increase (decrease) in net assets (143,406,035) (20,963,716)

NET ASSETS
 Beginning of period 338,072,203 359,035,919
-----------------------------------------------------------------------------------------------------------------------------
 End of period (including accumulated net investment loss of
 ($2,841,083) and ($4,573,224), respectively) $ 194,666,168 $ 338,072,203
=============================================================================================================================

See notes to financial statements.

18 | Annual Report | December 31, 2008

OLA | Old Mutual/Claymore Long-Short Fund

Financial HIGHLIGHTS |

 FOR THE PERIOD
 FOR THE FOR THE FOR THE AUGUST 25, 2005*
 YEAR ENDED YEAR ENDED YEAR ENDED THROUGH
PER SHARE OPERATING PERFORMANCE DECEMBER DECEMBER DECEMBER DECEMBER
FOR A COMMON SHARE OUTSTANDING THROUGHOUT THE PERIOD 31, 2008 31, 2007 31, 2006 31, 2005
-----------------------------------------------------------------------------------------------------------------------------
NET ASSET VALUE, BEGINNING OF PERIOD $ 17.79 $ 18.89 $ 18.80 $ 19.10(a)
-----------------------------------------------------------------------------------------------------------------------------
INCOME FROM INVESTMENT OPERATIONS
 Net investment income (loss) (b) 0.05 (0.10) 0.07 0.04
 Net realized and unrealized gain on investments, futures,
 options, Securities sold short, forwards and foreign
 currency (6.00) 0.60 1.62 0.10
-----------------------------------------------------------------------------------------------------------------------------
 Total from investment operations (5.95) 0.50 1.69 0.14
-----------------------------------------------------------------------------------------------------------------------------
COMMON SHARES' OFFERING EXPENSES CHARGED TO PAID-IN CAPITAL - - - (0.04)
-----------------------------------------------------------------------------------------------------------------------------
DISTRIBUTIONS TO COMMON SHAREHOLDERS
 From and in excess of net investment income (0.14) (1.60) (1.60) (0.40)
 Return of capital (1.46) - - -
-----------------------------------------------------------------------------------------------------------------------------
 Total distributions to common shareholders (1.60) (1.60) (1.60) (0.40)
-----------------------------------------------------------------------------------------------------------------------------
NET ASSET VALUE, END OF PERIOD $ 10.24 $ 17.79 $ 18.89 $ 18.80
=============================================================================================================================
MARKET VALUE, END OF PERIOD $ 7.98 $ 15.33 $ 18.33 $ 16.47
=============================================================================================================================
TOTAL INVESTMENT RETURN (C)
 Net asset value -35.09% 2.54% 9.36% 0.52%
 Market value -39.88% -8.45% 21.70% -15.76%

RATIOS AND SUPPLEMENTAL DATA

Net assets, end of period (thousands) $ 194,666 $ 338,072 $ 359,036 $ 357,292

RATIOS TO AVERAGE NET ASSETS, INCLUDING DIVIDEND EXPENSE ON
SECURITIES SOLD SHORT:
Total expense ratio 2.26% 2.81% 2.00% 1.58%(d)(e)
 Operating expense ratio 1.41% 1.50% 1.52% 1.34%(d)
 Dividends paid on securities sold short 0.85% 1.31% 0.48% 0.24%(d)(e)
Net investment income (loss) ratio 0.36% -0.55% 0.39% 0.75%(d)(e)
Portfolio turnover 223% 323% 248% 60%

* Commencement of investment operations.

(a) Before deduction of offering expenses charged to capital.

(b) Based on average shares outstanding during the period.

(c) Total investment return is calculated assuming a purchase of a common share at the beginning of the period and a sale on the last day of the period reported either at net asset value ("NAV") or market price per share. Dividends and distributions are assumed to be reinvested at NAV for NAV returns or the prices obtained under the Fund's Dividend Reinvestment Plan for market value returns. Total investment return does not reflect brokerage commissions. A return calculated for a period of less than one year is not annualized.

(d) Annualized.

(e) The expense ratio includes dividend payments made on securities sold short. During the approximate four month period from August 25, 2005 through December 31, 2005, nine securities sold short made two quarterly payments. The annualized ratios noted above have been adjusted such that these securities would only reflect the equivalent of four quarterly dividends per security. Had this adjustment not been made, the expense ratio would have been 1.65% and the net investment income ratio would have been 0.68%.

See notes to financial statements.

Annual Report | December 31, 2008 | 19

OLA | Old Mutual/Claymore Long-Short Fund

Notes to FINANCIAL STATEMENTS | DECEMBER 31, 2008

Note 1 - ORGANIZATION:
Old Mutual/Claymore Long-Short Fund (the "Fund") was organized as a Massachusetts business trust on December 3, 2004. The Fund is registered as a diversified, closed-end management investment company under the Investment Company Act of 1940, as amended (the"1940 Act").

The Fund's primary investment objective is to provide a high level of current income and current gains. The Fund's secondary investment objective is to provide long-term capital appreciation. The Fund seeks to achieve its investment objective by investing in a diversified portfolio of equity securities and by selling securities short in the S&P 500 Index that it believes will underperform relative to the average stock in the S&P 500. The Fund will also write (sell) call options on equity indices and, to a lesser extent, on individual securities held in the Fund's portfolio. The Fund may also employ a variety of other strategies involving futures and forward contracts and other derivative instruments in an attempt to enhance the Fund's investment returns. There can be no assurance that the Fund's investment objective will be achieved.

Note 2 - ACCOUNTING POLICIES:
The preparation of the financial statements in accordance with U.S. generally accepted accounting principles requires management to make estimates and assumptions that affect the reported amounts and disclosures in the financial statements. Actual results could differ from these estimates.

The following is a summary of significant accounting policies followed by the Fund.

(a) VALUATION OF INVESTMENTS AND DERIVATIVES Equity securities listed on an exchange are valued at the last reported sale price on the primary exchange on which they are traded. Equity securities for which there are no transactions on a given day are valued at the mean of the closing bid and asked prices. Securities traded on NASDAQ are valued at the NASDAQ Official Closing Price. Readily marketable securities listed on an exchange are valued at the last reported sale price on the primary exchange or in the principal over the counter ("OTC") market on which they are traded. Debt securities are valued by independent pricing services or dealers using the mean of the closing bid and asked prices for such securities or, if such prices are not available, at prices for securities of comparable maturity, quality and type. Equity index options are valued at the closing price on the primary exchange on which they are traded. Futures and options on future contracts are valued at the settlement price determined by the exchange on which they are traded. Forward exchange currency contracts are valued daily at current exchange rates. All other types of securities, including restricted securities, and securities for which market quotations are not readily available, are valued as determined in accordance with procedures established in good faith by the Board of Trustees. Short-term securities having a remaining maturity of sixty days or less at the time of purchase are valued at amortized cost, which approximates market value.

For those securities whose quotations or prices are not available, the valuations are determined in accordance with procedures established in good faith by the Board of Trustees. Valuations in accordance with these procedures are intended to reflect each security's (or asset's) "fair value". Such "fair value" is the amount that the Fund might reasonably expect to receive for the security (or asset) upon its current sale. Each such determination should be based on a consideration of all relevant factors, which are likely to vary from one pricing context to another. Examples of such factors may include, but are not limited to: (i) the type of security, (ii) the initial cost of the security,
(iii) the existence of any contractual restrictions on the security's disposition, (iv) the price and extent of public trading in similar securities of the issuer or of comparable companies, (v) quotations or evaluated prices from broker-dealers and/or pricing services, (vi) information obtained from the issuer, analysts, and/or the appropriate stock exchange (for exchange traded securities), (vii) an analysis of the company's financial statements, and (viii) an evaluation of the forces that influence the issuer and the market(s) in which the security is purchased and sold (e.g. the existence of pending merger activity, public offerings or tender offers that might affect the value of the security).

In September, 2006, the Financial Accounting Standards Board ("FASB") issued Statement of Financial Accounting Standard No.157,"Fair Valuation Measurements"("FAS 157"). This standard clarifies the definition of fair value for financial reporting, establishes a framework for measuring fair value and requires additional disclosures about the use of fair value measurements. FAS 157 establishes three different categories for valuations. Level 1 valuations are those based upon quoted prices in active markets. Level 2 valuations are those based upon quoted prices in inactive markets or based upon significant observable inputs (e.g. yield curves; benchmark interest rates; indices). Level 3 valuations are those based upon unobservable inputs (e.g. discounted cash flow analysis; non-market based methods used to determine fair valuation). Details of the valuations as of December 31, 2008 were as follows:

Valuations at December 31, 2008

DESCRIPTION SECURITIES DERIVATIVES TOTAL
--------------------------------------------------------------------------------
(value in $000s)
Assets:
Level 1 $ 243,766 $ - $ 243,766
Level 2 22,489 8,063 30,552
Level 3 - - -
--------------------------------------------------------------------------------
Total $ 266,255 $ 8,063 $ 274,318
================================================================================
Liabilities:
Level 1 $ 74,231 $ 3,830 $ 78,061
Level 2 - 4,920 4,920
Level 3 - - -
--------------------------------------------------------------------------------
Total $ 74,231 $ 8,750 $ 82,981
================================================================================

(b) INVESTMENT TRANSACTIONS AND INVESTMENT INCOME Investment transactions are accounted for on the trade date. Realized gains and losses on investments are determined on the identified cost basis. Dividend income is recorded net of applicable withholding taxes on the ex-dividend date and interest income is recorded on an accrual basis. Discounts or premiums on debt securities purchased are accreted or amortized to interest income over the lives of the respective securities using the effective interest method.

(c) FUTURES The Fund may engage in asset allocation strategies by purchasing or selling futures contracts on U.S. and foreign securities, indices and other assets. A futures contract provides for the future sale by one party and purchase by another party of a specified quantity of the security or other financial instrument at a specified price and time. A futures contract on an index is an agreement in which two parties agree to take or make delivery of an amount of cash equal to the difference between the value of the index at the close of the last trading day of the contract and the price at which the index contract was originally written. Upon entering into futures contracts, the Fund maintains an amount of cash or liquid securities with a value equal to a percentage of the contract amount with either a futures commission merchant pursuant to rules and regulations promulgated under the 1940 Act, as amended, or with its custodian in an account in the broker's name. This amount is known as initial margin. During the period the futures contract is open, payments are received from or made to the broker based upon changes in the value of the contract (the variation margin). The risk of loss associated with a futures contract is in excess of the variation margin reflected on the Statement of Assets and Liabilities. The Fund may use futures contracts in an attempt to enhance the Fund's

20 | Annual Report | December 31, 2008

OLA | Old Mutual/Claymore Long-Short Fund

NOTES TO FINANCIAL STATEMENTS | continued

investment returns, as an efficient way to gain broad market exposure with reduced transaction costs and/or to hedge against market and other risks in the Fund's portfolio. There are a number of risks associated with the use of futures contracts. A purchase or sale of a futures contract may result in losses in excess of the amount invested in the futures contract. If futures are used for hedging, there can be no guarantee that there will be a correlation between price movements in the hedging vehicle and in the Fund's portfolio securities being hedged.

(d) OPTIONS The Fund will opportunistically employ an option strategy in an attempt to generate gains from option premiums, enhance distributions payable to the Fund's shareholders and reduce overall portfolio risk. The Fund intends to pursue its options strategy primarily by writing call options on equity indices. As the writer (seller) of an equity index call option, the Fund would receive cash (the premium) from the purchaser of the option, and the purchaser would have the right to receive from the Fund any appreciation in the cash value of the index over the strike price upon exercise. If the purchaser exercises the index option sold by the Fund, the Fund would pay the purchaser the difference between the cash value of the index and the strike price. In effect, the Fund sells the potential appreciation in the value of the index above the strike price in exchange for the premium.

(e) SECURITIES SOLD SHORT The Fund may sell securities short. A short sale is a transaction in which the Fund sells securities it does not own, but rather has borrowed, in anticipation of a decline in the market price of the securities. The Fund is obligated to replace the borrowed securities at their market price at the time of replacement. The Fund's obligation to replace the securities borrowed in connection with a short sale will be fully secured by collateral held in a segregated account at the custodian. Short sales by the Fund involve certain risks and special considerations. Possible losses from short sales differ from losses that could be incurred from a purchase of a security because losses from a short sale may be unlimited, whereas losses from purchases cannot exceed the total amount invested.

Short equity securities listed on an exchange are valued at the last reported sale price on the primary exchange on which they are traded. Short equity securities for which there are no transactions on a given day are valued at the mean of the closing bid and asked prices. Short equity securities traded on NASDAQ are valued at the NASDAQ Official Closing Price. Readily marketable short equity securities listed on an exchange are valued at the last reported sale price on the primary exchange or in the principal over the counter ("OTC") market on which they are traded.

(f) CURRENCY TRANSLATION Assets and liabilities denominated in foreign currencies are translated into U.S. dollars at the mean of the bid and asked price of respective exchange rates on the last day of the period. Purchases and sales of investments denominated in foreign currencies are translated at the exchange rate on the date of the transaction.

Foreign exchange gain or loss resulting from holding of a foreign currency, expiration of a currency exchange contract, difference in exchange rates between the trade date and settlement date of an investment purchased or sold, and the difference between dividends actually received compared to the amount shown in a Fund's accounting records on the date of receipt are included as net realized gains or losses on foreign currency forwards and currency transactions in the Fund's Statement of Operations.

Foreign exchange gain or loss on assets and liabilities, other than investments, are included in unrealized appreciation (depreciation) on foreign currency translations.

(g) FORWARD EXCHANGE CURRENCY CONTRACTS The Fund may enter into forward exchange currency contracts in order to hedge its exposure to changes in foreign currency exchange rates on its foreign portfolio holdings, to hedge certain firm purchases and sales commitments denominated in foreign currencies and for investment purposes. A forward exchange currency contract is a commitment to purchase or sell a foreign currency on a future date at a negotiated forward rate. The gain or loss arising from the difference between the original contracts and the closing of such contracts are included in net realized gain or loss on foreign currency forwards and currency transactions on the Statement of Operations.

Fluctuations in the value of open forward exchange currency contracts are recorded for financial reporting purposes as unrealized appreciation and depreciation on foreign currency forwards and currency translation on the Statement of Operations.

The Fund's custodian will place and maintain cash not available for investment or other liquid assets in a separate account of the Fund having a value at least equal to the aggregate amount of the Fund's commitments under forward exchange currency contracts entered into with respect to position hedges.

Risks may arise from the potential inability of a counterparty to meet the terms of a contract and from unanticipated movements in the value of a foreign currency relative to the U.S. dollar. The face or contract amount, in U.S. dollars, reflects the total exposure the Fund has in that particular currency contract.

(h) DISTRIBUTIONS TO SHAREHOLDERS The Fund declares and pays quarterly dividends to common shareholders. Distributions to shareholders are recorded on the ex-dividend date. The amount and timing of distributions are determined in accordance with federal income tax regulations, which may differ from U.S. generally accepted accounting principles. These dividends consist of investment company taxable income, which generally includes qualified dividend income, ordinary income, short-term capital gains and premiums received on certain written options. Realized short-term capital gains and premiums received on certain options are considered ordinary income for tax purposes and will be reclassified at the Fund's fiscal year end on the Fund's Statement of Assets and Liabilities from accumulated net realized gains to accumulated net investment loss. Any net realized long-term capital gains will be distributed annually to common shareholders.

Note 3 - INVESTMENT ADVISORY AGREEMENT, SUB-ADVISORY AGREEMENT AND OTHER AGREEMENTS:
Pursuant to an Investment Advisory Agreement (the "Agreement") between the Fund and Claymore Advisors, LLC (the "Adviser"), the Adviser will furnish offices, necessary facilities and equipment, oversee the activities of Analytic Investors, LLC. ("Analytic" or the "Sub-Adviser"), provide personnel including certain officers required for its administrative management and pay the compensation of all officers and trustees of the Fund who are its affiliates. As compensation for these services, the Fund will pay the Adviser an annual fee, payable monthly, in an amount equal to 1.00% of the Fund's average daily total net assets.

Pursuant to a Sub-Advisory Agreement (the "Sub-Advisory Agreement") between the Fund, the Adviser and the Sub-Adviser, the Sub-Adviser under the supervision of the Fund's Board of Trustees and the Adviser, provides a continuous investment program for the Fund's portfolio; provides investment research, makes and executes recommendations for the purchase and sale of securities; and provides certain facilities and personnel, including certain officers required for its administrative management and pays the compensation of all officers and trustees of the Fund who are its affiliates. As compensation for its services, the Adviser pays

Annual Report | December 31, 2008 | 21

OLA | Old Mutual/Claymore Long-Short Fund | NOTES TO FINANCIAL STATEMENTS continued

the Sub-Adviser a fee, payable monthly, in an annual amount equal to 0.50% of the Fund's average daily total net assets. Analytic is an affiliate of Old Mutual (US) Holdings, Inc.

The Adviser provides Fund Administration services to the Fund. For its services, the Adviser receives a fund administration fee payable monthly at the annual rate set forth below as a percentage of the average daily total net assets of the Fund:

NET ASSETS RATE
--------------------------------------------------------------------------------
First $200,000,000 0.0275%
Next $300,000,000 0.0200%
Next $500,000,000 0.0150%
Over $1,000,000,000 0.0100%

The Bank of New York Mellon ("BNY") acts as the Fund's custodian, accounting agent, and transfer agent. As custodian, BNY is responsible for the custody of the Fund's assets. As accounting agent, BNY is responsible for maintaining the books and records of the Fund's securities and cash. As transfer agent, BNY is responsible for performing transfer agency services for the Fund.

Certain officers and trustees of the Fund are also officers and directors of the Adviser or the Sub-Adviser. The Fund does not compensate its officers or trustees who are officers of the aforementioned firms.

Note 4 - FEDERAL INCOME TAXES:
The Fund intends to comply with the requirements of Subchapter M of the Internal Revenue Code of 1986, as amended, applicable to regulated investment companies. Accordingly, no provision for U.S. federal income taxes is required. In addition, by distributing substantially all of its ordinary income and long-term capital gains, if any, during each calendar year, the Fund intends not to be subject to U.S. federal excise tax.

Due to inherent differences in the recognition of income, expenses, and realized gains/losses under U.S. generally accepted accounting principles and federal income tax purposes, permanent differences between book and tax basis reporting have been identified and appropriately reclassified on the Statement of Assets and Liabilities. A permanent book and tax difference relating to a distribution reclass in the amount of $2,755,313 was reclassified from accumulated net investment loss to accumulated net realized loss. Also permanent book and tax differences relating to losses on foreign currency transactions in the amount of $13,238,546 were reclassified from accumulated net realized loss to accumulated net investment loss. Additionally, a permanent book and tax difference relating to capital gain and return of capital distributions received from real estate investment trusts totaling $150,934 was reclassified from accumulated net realized loss to accumulated net investment loss. Finally, a permanent book and tax difference relating to net operating losses in the amount of $14,152,603 was reclassified from accumulated net investment loss to capital.

Capital losses and foreign currency transactions incurred after October 31 ("post-October" losses) within the taxable year are deemed to arise on the first business day of the Fund's next taxable year. The Fund incurred and elected to defer capital losses and foreign currency related losses from 2008 in the amount of $10,379,228 and $1,619,801, respectively.

Information on the tax components of investments, excluding short sales transactions and excluding written options, and net assets as of December 31, 2008 is as follows:

 NET TAX
 COST OF NET TAX UNREALIZED
 INVESTMENTS GROSS TAX GROSS TAX UNREALIZED APPRECIATION ON
 FOR TAX UNREALIZED UNREALIZED DEPRECIATION ON DERIVATIVES AND
 PURPOSES APPRECIATION DEPRECIATION INVESTMENTS FOREIGN CURRENCY
--------------------------------------------------------------------------------
$368,304,001 $ 3,256,070 $(105,304,809) $ (102,048,739) $ 2,256,891

Information on the tax components of securities sold short as of December 31, 2008 is as follows:

 NET TAX
 PROCEEDS FROM UNREALIZED
 SECURITIES GROSS TAX GROSS TAX APPRECIATION
SOLD SHORT FOR UNREALIZED UNREALIZED ON SECURITIES
 TAX PURPOSES APPRECIATION DEPRECIATION SOLD SHORT
--------------------------------------------------------------------------------
$ 87,787,981 $ 17,404,324 $ (3,847,742) $ 13,556,582

Tax components of the following balances as of December 31, 2008 and 2007 are as follows:

 DECEMBER 31, 2008 DECEMBER 31, 2007
--------------------------------------------------------------------------------
Accumulated Net Investment Loss $ (1,619,801) $ (4,518,893)
Accumulated Capital and Other Losses $ (37,913,175) -

For the years ended December 31, 2008 and 2007, the tax character of distributions paid to shareholders as reflected in the Statement of Changes in Net Assets, was as follows:

DISTRIBUTIONS PAID FROM: 2008 2007
--------------------------------------------------------------------------------
Ordinary Income $ 2,749,600 $ 26,761,014
Capital Gain 5,713 3,647,370
Return of Capital 27,653,071 -
--------------------------------------------------------------------------------
 $ 30,408,384 $ 30,408,384
--------------------------------------------------------------------------------

At December 31, 2008, for federal income tax purposes, the Fund had a capital loss carryforward of $27,533,947 available to offset possible future capital gains. The capital loss carryforward is set to expire December 31, 2016.

The Fund adopted the provisions of Financial Accounting Standards Board ("FASB") Interpretation No.48 ("FIN 48") Accounting for Uncertainty in Income Taxes on December 31, 2007. FIN 48 sets forth a minimum threshold for financial statement recognition of the benefit of a tax position taken or expected to be taken in a tax return. The implementation of FIN 48 did not result in any unrecognized tax benefits in the accompanying financial statements.

Tax years for 2005, 2006 and 2007 are still subject to examination by major jurisdictions.

Note 5 - INVESTMENT TRANSACTIONS AND OPTIONS WRITTEN:
For the year ended December 31, 2008, purchases and sales of investments, excluding written options with maturities of less than one year and short-term securities, were $733,135,606 and $775,263,161, respectively.

The Fund entered into written call option contracts during the year ended December 31, 2008. Details of the transactions were as follows:

 NUMBER OF
 CONTRACTS PREMIUMS RECEIVED
--------------------------------------------------------------------------------
Options outstanding, beginning of year 6,550 $ 8,372,488
Options written, during the year 160,248 202,896,631
Options expired, during the year (28,939) (24,463,126)
Options closed, during the year (133,122) (181,242,992)
--------------------------------------------------------------------------------
Options outstanding, end of year 4,737 $ 5,563,001
--------------------------------------------------------------------------------

22 | Annual Report | December 31, 2008

OLA | Old Mutual/Claymore Long-Short Fund | NOTES TO FINANCIAL STATEMENTS continued

Note 6 - DERIVATIVES:
At December 31, 2008, the following futures contracts were outstanding:

 UNREALIZED
 NUMBER OF APPRECIATION
LONG CONTRACTS CONTRACTS (DEPRECIATION)
-------------------------------------------------------------------------------------------------------------
90 Day Euro$ IMM - June 2009
(Current notional value of $247,175 per contract) 461 $ 2,005,350

90 Day Euro$ IMM - September 2009
(Current notional value of $246,863 per contract) 461 610,813

Amsterdam Exchanges Index - January 2009
(Current notional value of 49,270 Euro per contract) 226 42,172

Australia SPI 200 Index - March 2009
(Current notional value of 93,650 Australian dollars per contract) 287 1,080,262

Canada S&P/TSE 60 Index - March 2009
(Current notional value of 107,980 Canadian dollars per contract) 124 724,648

Eurozone Dow Jones Euro STOXX 50 - March 2009
(Current notional value of 24,500 Euro per contract) 80 32,178

Italy S&P/MIB Index - March 2009
(Current notional value of 97,110 Euro per contract) 107 229,999

Sweden QMXS30 - January 2009
(Current notional value of 65,900 Swedish Krona per contract) 1,165 (87,966)

U.S. CBOE Volatility Index - January 2009
(Current notional value of $41,940 per contract) 85 (998,502)
-------------------------------------------------------------------------------------------------------------
 2,996 $ 3,638,954
-------------------------------------------------------------------------------------------------------------

 UNREALIZED
 NUMBER OF APPRECIATION
SHORT CONTRACTS CONTRACTS (DEPRECIATION)
-------------------------------------------------------------------------------------------------------------
Japan TOPIX Index - March 2009
(Current notional value of 8,620,000 Japanese Yen per contract) 186 $ (931,330)

Spain IBEX 35 Index - January 2009
(Current notional value of 91,130 Euro per contract) 95 (82,985)

U.S. S&P 500 - March 2009
(Current notional value of $45,005 per contract) 258 (332,175)

United Kingdom FTSE 100 Index - March 2009
(Current notional value of 43,900 Pound Sterling per contract) 252 (371,140)
-------------------------------------------------------------------------------------------------------------
 791 $ (1,717,630)
-------------------------------------------------------------------------------------------------------------
 3,787 $ 1,921,324
-------------------------------------------------------------------------------------------------------------

All notional values are denominated in local currencies.

At December 31, 2008, the following forward exchange currency contracts were outstanding:

 LOCAL UNREALIZED
 CURRENCY APPRECIATION
LONG CONTRACTS VALUE (DEPRECIATION)
-------------------------------------------------------------------------------------------------------------
Australian Dollar, 6,000,000 expiring 3/18/09 4,154,426 $ 162,926
Japanese Yen, 3,100,000,000 expiring 3/18/09 34,249,128 370,828
New Zealand Dollar, 61,000,000 expiring 3/18/09 35,344,756 2,044,856
Swedish Krona, 140,000,000 expiring 3/18/09 17,687,353 171,808
-------------------------------------------------------------------------------------------------------------
 $ 2,750,418
-------------------------------------------------------------------------------------------------------------

SHORT CONTRACTS
-------------------------------------------------------------------------------------------------------------
Canadian Dollar, 39,000,000 expiring 3/18/09 31,596,500 $ 157,286
Euro, 26,000,000 expiring 3/18/09 36,051,111 (1,729,291)
Norwegian Krone, 60,000,000 expiring 3/18/09 8,530,736 87,229
Pound Sterling, 6,000,000 expiring 3/18/09 8,613,272 342,148
Swiss Franc, 4,000,000 expiring 3/18/09 3,761,010 (386,508)
-------------------------------------------------------------------------------------------------------------
 $ (1,529,136)
-------------------------------------------------------------------------------------------------------------
 $ 1,221,282
-------------------------------------------------------------------------------------------------------------

Note 7 - CAPITAL:

COMMON SHARES
The Fund has an unlimited amount of common shares, $0.01 par value, authorized and 19,005,240 issued and outstanding.

There were no transactions in common shares during the year ended December 31, 2008 or the year ended December 31, 2007.

At December 31, 2008, Claymore Securities, Inc. owned 5,476 shares.

Note 8 - INDEMNIFICATIONS:
In the normal course of business, the Fund enters into contracts that contain a variety of representations, which provide general indemnifications. The Fund's maximum exposure under these arrangements is unknown, as this would require future claims that may be made against the Fund that have not yet occurred. However, the Fund expects the risk of loss to be remote.

Note 9 - ACCOUNTING PRONOUNCEMENT:
In March 2008, the FASB issued Statement of Financial Accounting Standard No.161 ("SFAS No.161"), "Disclosures about Derivative Instruments and Hedging Activities." This standard is intended to enhance financial statement disclosures for derivative instruments and hedging activities and enable investors to understand: a) how and why a fund uses derivative instruments, b) how derivatives instruments and related hedge fund items are accounted for, and
c) how derivative instruments and related hedge items affect a fund's financial position, results of operations and cash flows. SFAS No.161 is effective for financial statements issued for fiscal years and interim periods beginning after November 15, 2008. As of December 31, 2008, management does not believe the adoption of SFAS No.161 will impact the financial statement amounts; however, additional footnote disclosures may be required about the use of derivative instruments and hedging items.

Annual Report | December 31, 2008 | 23

OLA | Old Mutual/Claymore Long-Short Fund

Report of INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM |

TO THE SHAREHOLDERS AND BOARD OF TRUSTEES OF
OLD MUTUAL/CLAYMORE LONG-SHORT FUND

We have audited the accompanying statement of assets and liabilities of Old Mutual/Claymore Long-Short Fund (the "Fund"), including the portfolio of investments, as of December 31, 2008, and the related statement of operations for the year then ended, the statements of changes in net assets for each of the two years in the period then ended, and the financial highlights for each of the three years in the period then ended and for the period from August 25, 2005 (commencement of investment operations) through December 31, 2005. These financial statements and financial highlights are the responsibility of the Fund's management. Our responsibility is to express an opinion on these financial statements and financial highlights based on our audits.

We conducted our audits in accordance with the standards of the Public Company Accounting Oversight Board (United States). Those standards require that we plan and perform the audits to obtain reasonable assurance about whether the financial statements and financial highlights are free of material misstatement. We were not engaged to perform an audit of the Fund's internal control over financial reporting. Our audits included consideration of internal control over financial reporting as a basis for designing audit procedures that are appropriate in the circumstances, but not for the purpose of expressing an opinion on the effectiveness of the Fund's internal control over financial reporting. Accordingly, we express no such opinion. An audit also includes examining, on a test basis, evidence supporting the amounts and disclosures in the financial statements and financial highlights, assessing the accounting principles used and significant estimates made by management, and evaluating the overall financial statement presentation. Our procedures included confirmation of securities owned as of December 31, 2008, by correspondence with the Fund's custodian and brokers. We believe that our audits provide a reasonable basis for our opinion.

In our opinion, the financial statements and financial highlights referred to above present fairly, in all material respects, the financial position of Old Mutual/Claymore Long-Short Fund as of December 31, 2008, and the results of its operations for the year then ended, the changes in its net assets for each of the two years in the period then ended, and the financial highlights for each of the three years in the period then ended and for the period from August 25, 2005 (commencement of investment operations) through December 31, 2005, in conformity with U.S. generally accepted accounting principles.

 /s/ Ernst & Young LLP

Chicago, Illinois
February 18, 2009

24 | Annual Report | December 31, 2008

OLA | Old Mutual/Claymore Long-Short Fund

Supplemental INFORMATION | (unaudited)

FEDERAL INCOME TAX INFORMATION
Subchapter M on the Internal Revenue Code of 1986, as amended, requires the Fund to advise shareholders within 60 days of the Fund's tax year end as to the federal tax status of dividends and distributions received by shareholders during such tax period. The Fund hereby designates $5,713 as long-term capital gains according to IRC Section 852(b)(3)(C).

In January 2009, you will be advised on IRS Form 1099 DIV or substitute 1099 DIV as to the federal tax status of the distributions received by you in the calendar year 2008.

RESULTS OF SHAREHOLDER VOTES
The Annual Meeting of Shareholders of the Fund was held on July 21, 2008. Common shareholders voted on the election of Trustees.

With regard to the election of the following Class III Trustees by common shareholders of the Fund:

 # OF SHARES # OF SHARES
 IN FAVOR WITHHELD
--------------------------------------------------------------------------------
L. Kent Moore 16,093,700 422,450
Ronald A. Nyberg 16,095,871 420,280
Ronald E. Toupin, Jr. 16,093,634 422,517

The other Trustees of the Fund whose terms did not expire in 2008 are Randall C. Barnes, Steven D. Cosler, Robert M. Hamje, Matthew J. Appelstein and Nicholas Dalmaso.

Annual Report | December 31, 2008 | 25

OLA | Old Mutual/Claymore Long-Short Fund | SUPPLEMENTAL INFORMATION (unaudited) continued

TRUSTEES
The Trustees of the Old Mutual/Claymore Long-Short Fund and their principal occupations during the past five years:

 NUMBER OF
NAME, ADDRESS,* YEAR OF TERM OF OFFICE** PRINCIPAL OCCUPATION DURING PORTFOLIOS IN THE
BIRTH AND POSITION(S) AND LENGTH OF THE PAST FIVE YEARS AND FUND COMPLEX*** OTHER DIRECTORSHIPS
HELD WITH REGISTRANT TIME SERVED OTHER AFFILIATIONS OVERSEEN BY TRUSTEE HELD BY TRUSTEE
------------------------------------------------------------------------------------------------------------------------------------
INDEPENDENT TRUSTEES:
------------------------------------------------------------------------------------------------------------------------------------
Randall C. Barnes Since 2005 Private Investor (2001-present). 43 None.
Year of Birth: 1951 Formerly, Senior Vice President &
Trustee Treasurer, PepsiCo. Inc. (1993-1997),
 President, Pizza Hut International
 (1991-1993) and Senior Vice President,
 Strategic Planning and New Business
 Development (1987-1990) of PepsiCo,
 Inc. (1987-1997).
------------------------------------------------------------------------------------------------------------------------------------
Steven D. Cosler Since 2005 Formerly, President, Chief Executive 2 Director, SXC
Year of Birth: 1955 Officer and Director of Priority Health Solutions,
Trustee Healthcare Corp. (2002-2005). Formerly, Corp.
 President and Chief Operating Officer
 of Priority Healthcare Corp.
 (2001-2002). Formerly, Executive Vice
 President and Chief Operating Officer
 of Priority Healthcare Corp.
 (2000-2001).
------------------------------------------------------------------------------------------------------------------------------------
Robert M. Hamje Since 2005 Formerly, President and Chief 2 Trustee, Old
Year of Birth: 1942 Investment Officer of TRW Investment Mutual Advisor
Trustee Management Co. (1990-2003). Mutual Funds.
------------------------------------------------------------------------------------------------------------------------------------
L. Kent Moore Since 2005 Partner at WilSource Enterprise 2 Trustee, Old
Year of Birth: 1955 (December 2005-Present). Previously, Mutual Advisor
Trustee Managing Director High Sierra Energy Mutual Funds.
 L.P., (2004-2005). Formerly, Portfolio
 Manager and Vice President of Janus
 Capital Corp. (2000-2002) and Senior
 Analyst/Portfolio Manager of Marsico
 Capital Management (1997-1999).
------------------------------------------------------------------------------------------------------------------------------------
Ronald A. Nyberg Since 2005 Partner of Nyberg & Cassioppi, LLC, a 46 None.
Year of Birth: 1953 law firm specializing in corporate law,
Trustee estate planning and business
 transactions (2000-present). Formerly,
 Executive Vice President, General
 Counsel and Corporate Secretary of Van
 Kampen Investments (1982-1999).
------------------------------------------------------------------------------------------------------------------------------------
Ronald E. Toupin, Jr. Since 2005 Retired. Formerly, Vice President, 43 None.
Year of Birth: 1958 Manager and Portfolio Manager of Nuveen
Trustee Asset Management (1998-1999), Vice
 President of Nuveen Investment Advisory
 Corp. (1992-1999), Vice President and
 Manager of Nuveen Unit Investment
 Trusts (1991-1999), and Assistant Vice
 President and Portfolio Manager of
 Nuveen Unit Investment Trusts
 (1988-1999), each of John Nuveen & Co.,
 Inc. (1982-1999).
------------------------------------------------------------------------------------------------------------------------------------
INTERESTED TRUSTEES:
------------------------------------------------------------------------------------------------------------------------------------
Matthew J. Appelstein+ Since 2005 Senior Vice President of Product 2 None.
Year of Birth: 1961 Strategy and Retirement Solutions
Trustee Planning, Director of Investment
 Services, Old Mutual Asset Management
 (2003-present). Formerly, Senior Vice
 President of Consulting Relationships,
 Fidelity Management Trust
 Co. (1998-2003).
------------------------------------------------------------------------------------------------------------------------------------
Nicholas Dalmaso++ Since 2005 Attorney. Formerly, Senior Managing 45 None.
Year of birth: 1965 Director and Chief Administrative
Trustee Officer (2007-2008) and General Counsel
 (2001-2007) of Claymore Advisors, LLC
 and Claymore Securities, Inc.
 (2001-2008). Formerly, Assistant
 General Counsel, John Nuveen and
 Company, Inc. (1999-2000). Former Vice
 President and Associate General Counsel
 of Van Kampen Investments, Inc.
 (1992-1999).
------------------------------------------------------------------------------------------------------------------------------------

* Address for all Trustees unless otherwise noted: 2455 Corporate West Drive, Lisle, IL 60532

** After a Trustee's initial term, each Trustee is expected to serve a three-year term concurrent with the class of Trustees for which he serves:

- Messrs. Appelstein and Barnes, as Class I Trustees, are expected to stand for re-election at the Fund's 2009 annual meeting of shareholders.

- Messrs. Cosler, Dalmaso and Hamje, as Class II Trustees, are expected to stand for re-election at the Fund's 2010 annual meeting of shareholders.

- Messrs. Moore, Nyberg and Toupin, as Class III Trustees, are expected to stand for re-election at the Fund's 2011 annual meeting of shareholders.

*** The Claymore Fund Complex consists of U.S. registered investment companies advised or serviced by Claymore Advisors, LLC or Claymore Securities, Inc. The Claymore Fund Complex is overseen by multiple Boards of Trustees.

+ Mr. Appelstein is an "interested person"(as defined in Section 2(a)(19) of the 1940 Act) of the Fund because of his position as an officer of Old Mutual Asset Management, the parent company of the Fund's Sub-Adviser.

++ Mr. Dalmaso is an "interested person"(as defined in section 2(a)(19) of the 1940 Act) of the Fund because of his former position as an officer of, and his equity ownership in, the Fund's Investment Adviser and certain of its affiliates.

26 | Annual Report | December 31, 2008

OLA | Old Mutual/Claymore Long-Short Fund | SUPPLEMENTAL INFORMATION (unaudited) continued

OFFICERS
The Officers of the Old Mutual/Claymore Long-Short Fund and their principal occupations during the past five years:

NAME, ADDRESS*, YEAR OF BIRTH AND TERM OF OFFICE** AND PRINCIPAL OCCUPATION DURING THE PAST FIVE YEARS
POSITION(S) HELD WITH REGISTRANT LENGTH OF TIME SERVED AND OTHER AFFILIATIONS
------------------------------------------------------------------------------------------------------------------------------------
OFFICERS:
------------------------------------------------------------------------------------------------------------------------------------
J. Thomas Futrell Since 2008 Senior Managing Director and Chief Investment Officer of Claymore
Year of birth: 1955 Advisors, LLC and Claymore Securities, Inc. (2008-present). Chief
Chief Executive Officer Executive Officer of certain other funds in the Fund Complex.
 Formerly, Managing Director of Research, Nuveen Asset Management
 (2000-2007).
------------------------------------------------------------------------------------------------------------------------------------
Kevin M. Robinson Since 2008 Senior Managing Director and General Counsel of Claymore Advisors,
Year of birth: 1959 LLC, Claymore Securities, Inc. and Claymore Group Inc. (2007-present).
Chief Legal Officer Chief Legal Officer of certain other funds in the Fund Complex.
 Formerly, Associate General Counsel and Assistant Corporate Secretary
 of NYSE Euronext, Inc. (2000-2007).
------------------------------------------------------------------------------------------------------------------------------------
Steven M. Hill Since 2005 Senior Managing Director of Claymore Advisors, LLC and Claymore
Year of Birth: 1964 Securities, Inc. (2005-present). Previously, Chief Financial Officer
Chief Accounting Officer, of Claymore Group Inc. (2005-2006). Managing Director of Claymore
Chief Financial Officer and Advisors, LLC and Claymore Securities, Inc. (2003-2005). Treasurer of
Treasurer Henderson Global Funds and Operations Manager for Henderson Global
 Investors (North America) Inc. (2002-2003); Managing Director, Front
 Point Partners LLC (2001-2002); Vice President, Nuveen Investments
 (1999-2001); Chief Financial Officer, Skyline Asset Management LP
 (1999); Vice President, Van Kampen Investments and Assistant
 Treasurer, Van Kampen mutual funds (1989-1999).
------------------------------------------------------------------------------------------------------------------------------------
Matthew J. Patterson Since 2006 Vice President; Assistant General Counsel of Claymore Group Inc.
Year of Birth: 1971 (2006-present). Secretary of certain funds in the Fund Complex.
Secretary Previously, Chief Compliance Officer and Clerk, The Preferred Group of
 Mutual Funds (2005-2006); Chief Compliance Officer and Secretary,
 Caterpillar Investment Management Ltd (2005-2006); Securities Counsel,
 Caterpillar Inc. (2004-2006); Associate, Skadden, Arps, Slate, Meagher
 & Flom LLP (2002-2004).
------------------------------------------------------------------------------------------------------------------------------------
Bruce Saxon Since 2006 Vice President-Fund Compliance Officer of Claymore Group Inc. (Feb
Year of Birth: 1957 2006-present). Previously, Chief Compliance Officer/Assistant
Chief Compliance Officer Secretary of Harris Investment Management, Inc. (2003-2006).
 Director-Compliance of Harrisdirect LLC (1999-2003).
------------------------------------------------------------------------------------------------------------------------------------

* Address for all Officers: 2455 Corporate West Drive, Lisle, IL 60532

** Officers serve at the pleasure of the Board of Trustees and until his or her successor is appointed and qualified or until his or her earlier resignation or removal.

Annual Report | December 31, 2008 | 27

OLA | Old Mutual/Claymore Long-Short Fund

Dividend Reinvestment PLAN | (unaudited)

Unless the registered owner of common shares elects to receive cash by contacting the Bank of New York Mellon (the "Plan Administrator"), all dividends declared on common shares of the Fund will be automatically reinvested by the Plan Administrator for shareholders in the Fund's Dividend Reinvestment Plan (the "Plan"), in additional common shares of the Fund. Participation in the Plan is completely voluntary and may be terminated or resumed at any time without penalty by notice if received and processed by the Plan Administrator prior to the dividend record date; otherwise such termination or resumption will be effective with respect to any subsequently declared dividend or other distribution. Some brokers may automatically elect to receive cash on your behalf and may re-invest that cash in additional common shares of the Fund for you. If you wish for all dividends declared on your common shares of the Fund to be automatically reinvested pursuant to the Plan, please contact your broker.

The Plan Administrator will open an account for each common shareholder under the Plan in the same name in which such common shareholder's common shares are registered. Whenever the Fund declares a dividend or other distribution (together, a "Dividend") payable in cash, non-participants in the Plan will receive cash and participants in the Plan will receive the equivalent in common shares. The common shares will be acquired by the Plan Administrator for the participants' accounts, depending upon the circumstances described below, either
(i) through receipt of additional unissued but authorized common shares from the Fund ("Newly Issued Common Shares") or (ii) by purchase of outstanding common shares on the open market ("Open-Market Purchases") on the New York Stock Exchange or elsewhere. If, on the payment date for any Dividend, the closing market price plus estimated brokerage commission per common share is equal to or greater than the net asset value per common share, the Plan Administrator will invest the Dividend amount in Newly Issued Common Shares on behalf of the participants. The number of Newly Issued Common Shares to be credited to each participant's account will be determined by dividing the dollar amount of the Dividend by the net asset value per common share on the payment date; provided that, if the net asset value is less than or equal to 95% of the closing market value on the payment date, the dollar amount of the Dividend will be divided by 95% of the closing market price per common share on the payment date. If, on the payment date for any Dividend, the net asset value per common share is greater than the closing market value plus estimated brokerage commission, the Plan Administrator will invest the Dividend amount in common shares acquired on behalf of the participants in Open-Market Purchases.

If, before the Plan Administrator has completed its Open-Market Purchases, the market price per common share exceeds the net asset value per common share, the average per common share purchase price paid by the Plan Administrator may exceed the net asset value of the common shares, resulting in the acquisition of fewer common shares than if the Dividend had been paid in Newly Issued Common Shares on the Dividend payment date. Because of the foregoing difficulty with respect to Open-Market Purchases, the Plan provides that if the Plan Administrator is unable to invest the full Dividend amount in Open-Market Purchases during the purchase period or if the market discount shifts to a market premium during the purchase period, the Plan Administrator may cease making Open-Market Purchases and may invest the uninvested portion of the Dividend amount in Newly Issued Common Shares at net asset value per common share at the close of business on the Last Purchase Date provided that, if the net asset value is less than or equal to 95% of the then current market price per common share; the dollar amount of the Dividend will be divided by 95% of the market price on the payment date.

The Plan Administrator maintains all shareholders' accounts in the Plan and furnishes written confirmation of all transactions in the accounts, including information needed by shareholders for tax records. Common shares in the account of each Plan participant will be held by the Plan Administrator on behalf of the Plan participant, and each shareholder proxy will include those shares purchased or received pursuant to the Plan. The Plan Administrator will forward all proxy solicitation materials to participants and vote proxies for shares held under the Plan in accordance with the instruction of the participants.

There will be no brokerage charges with respect to common shares issued directly by the Fund. However, each participant will pay a pro rata share of brokerage commission incurred in connection with Open-Market Purchases. The automatic reinvestment of Dividends will not relieve participants of any Federal, state or local income tax that may be payable (or required to be withheld) on such Dividends.

The Fund reserves the right to amend or terminate the Plan. There is no direct service charge to participants with regard to purchases in the Plan; however, the Fund reserves the right to amend the Plan to include a service charge payable by the participants.

All correspondence or questions concerning the Plan should be directed to the Plan Administrator, BNY Mellon Shareowner Services, PO Box 358015, Pittsburgh, PA 15252-8015, Phone Number:(866) 488-3559.

28 | Annual Report | December 31, 2008

This Page Intentionally Left Blank.

This Page Intentionally Left Blank.

OLA | Old Mutual/Claymore Long-Short Fund

Fund INFORMATION |

BOARD OF TRUSTEES

Matthew J. Appelstein*

Randall C. Barnes

Steven D. Cosler

Nicholas Dalmaso**

Robert M. Hamje

L. Kent Moore

Ronald A. Nyberg

Ronald E. Toupin, Jr.

* Trustee is an "interested person" of the Fund as defined in the Investment Company Act of 1940, as amended.

** Trustee is an "interested person" of the Fund as defined in the Investment Company Act of 1940, as amended, as a result of his former position as an officer of, and his equity ownership in, the Fund's Investment Adviser and certain of its affiliates.

OFFICERS
J. Thomas Futrell
Chief Executive Officer

Kevin Robinson
Chief Legal Officer

Steven M. Hill
Chief Accounting Officer, Chief
Financial Officer and Treasurer

Matthew J. Patterson
Secretary

Bruce Saxon
Chief Compliance Officer

INVESTMENT ADVISER
Claymore Advisors, LLC
Lisle, Illinois

INVESTMENT SUB-ADVISER
Analytic Investors, LLC
Los Angeles, California

ADMINISTRATOR
Claymore Advisors, LLC
Lisle, Illinois

ACCOUNTING AGENT, CUSTODIAN AND TRANSFER AGENT
The Bank of New York Mellon
New York, New York

LEGAL COUNSEL
Skadden, Arps, Slate,
Meagher & Flom LLP
Chicago, Illinois

INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM
Ernst & Young LLP
Chicago, Illinois

PRIVACY PRINCIPLES OF OLD MUTUAL/CLAYMORE LONG-SHORT FUND FOR SHAREHOLDERS The Fund is committed to maintaining the privacy of its shareholders and to safeguarding its non-public personal information. The following information is provided to help you understand what personal information the Fund collects, how we protect that information and why, in certain cases, we may share information with select other parties.

Generally, the Fund does not receive any non-public personal information relating to its shareholders, although certain non-public personal information of its shareholders may become available to the Fund. The Fund does not disclose any non-public personal information about its shareholders or former shareholders to anyone, except as permitted by law or as is necessary in order to service shareholder accounts (for example, to a transfer agent or third party administrator).

The Fund restricts access to non-public personal information about the shareholders to Claymore Advisors, LLC employees with a legitimate business need for the information. The Fund maintains physical, electronic and procedural safeguards designed to protect the non-public personal information of its shareholders.

QUESTIONS CONCERNING YOUR SHARES OF OLD MUTUAL/CLAYMORE LONG-SHORT FUND?

o If your shares are held in a Brokerage Account, contact your Broker.

o If you have physical possession of your shares in certificate form, contact the Fund's Custodian and Transfer Agent:

The Bank of New York Mellon, 101 Barclay 11E, New York, New York 12086 (866) 488-3559

This report is sent to shareholders of Old Mutual/Claymore Long-Short Fund for their information. It is not a Prospectus, circular or representation intended for use in the purchase or sale of shares of the Fund or of any securities mentioned in this report.

A description of the Fund's proxy voting policies and procedures related to portfolio securities is available without charge, upon request, by calling the Fund at (866) 882-0688.

Information regarding how the Fund voted proxies for portfolio securities, if applicable, during the most recent 12-month period ended June 30, is also available, without charge and upon request by calling (866) 882-0688 or by accessing the Fund's Form N-PX on the U.S. Securities and Exchange Commission's ("SEC") website at www.sec.gov or www.claymore.com .

The Fund files its complete schedule of portfolio holdings with the SEC for the first and third quarters of each fiscal year on Form N-Q. The Fund's Form N-Q is available on the SEC website at www.sec.gov or www.claymore.com. The Fund's Form N-Q may also be viewed and copied at the SEC's Public Reference Room in Washington, DC; information on the operation of the Public Reference Room may be obtained by calling (800) SEC-0330 or at www.sec.gov .

In August 2008, the Fund submitted a CEO annual certification to the NYSE in which the Fund's principal executive officer certified that he was not aware, as of the date of the certification, of any violation by the Fund of the NYSE's Corporate Governance listing standards. In addition, as required by Section 302 of the Sarbanes-Oxley Act of 2002 and related SEC rules, the Fund's principal executive and principal financial officers have made quarterly certifications, included in filings with the SEC on Forms N-CSR and N-Q, relating to, among other things, the Fund's disclosure controls and procedures and internal control over financial reporting.

Notice is hereby given in accordance with Section 23(c) of the Investment Company Act of 1940 that the Fund may from time to time purchase its shares of common stock in the open market.

Annual Report | December 31, 2008 | 31

OLA | Old Mutual/Claymore Long-Short Fund

About the FUND MANAGER |

ANALYTIC INVESTORS, LLC
Analytic Investors specializes in the application of systematic investment processes to evaluate and exploit opportunities in the global equity, fixed income and derivative securities markets. Based in Los Angeles and wholly owned by Old Mutual plc, Analytic employs 35 professionals and manages more than $8 billion. The firm manages a range of traditional, long-only equity products as well as a number of absolute return strategies. The firm was founded in 1970 and, since that time, has focused on delivering valued-added, risk-controlled investment strategies to its range of institutional, fund-of-fund, and high net worth clients.

INVESTMENT PHILOSOPHY
Analytic's philosophy is anchored in the conviction that the systematic application of quantitative techniques to assess opportunity has the potential to deliver quality, risk-adjusted performance, regardless of market cycle. Analytic's quantitative methods bring together the best attributes of individual security selection and unbiased portfolio modeling, yielding a management style that is both disciplined and responsive.

INVESTMENT PROCESS
Analytic's innovative research seeks to uncover the factors that are driving performance and are likely to be important going forward. Two core beliefs underlie the firm's investment process:

o The attractiveness of every security is determined by a multitude of factors that can be measured.

o The desirability of a security's characteristics change with economic conditions.

Sophisticated quantitative techniques enable Analytic to simultaneously analyze a variety of unique characteristics - such as relative valuation, growth potential, historical returns, liquidity and risk - in an effort to identify and exploit opportunities. Analytic uses thorough statistical analysis in an attempt to identify the merits of each security as well as the relationships between each security's measurable characteristics that may be driving its performance.

Analytic's proprietary multi-factor return models are applied in a risk-controlled environment. The firm's highly evolved and successful approach, supported by the research efforts of its investment team, capitalizes on opportunity while neutralizing systematic market exposure and overall risk.

CLAYMORE SECURITIES, INC.
2455 Corporate West Drive
Lisle, IL 60532
Member FINRA/SIPC
(02/09)

OLA
LISTED
NYSE(R)

OLA-AR-1208

NOT FDIC-INSURED | NOT BANK-GUARANTEED | MAY LOSE VALUE

ITEM 2. CODE OF ETHICS.

(a) The registrant has adopted a code of ethics (the "Code of Ethics") that applies to its principal executive officer, principal financial officer, principal accounting officer or controller, or persons performing similar functions.

(b) No information need be disclosed pursuant to this paragraph.

(c) The registrant has not amended its Code of Ethics during the period covered by the shareholder report presented in Item 1 hereto.

(d) The registrant has not granted a waiver or an implicit waiver to its principal executive officer, principal financial officer, principal accounting officer or controller, or persons performing similar functions from a provision of its Code of Ethics during the period covered by this report.

(e) Not applicable.

(f) (1) The registrant's Code of Ethics is attached hereto as an exhibit.

(2) Not applicable.

(3) Not applicable.

ITEM 3. AUDIT COMMITTEE FINANCIAL EXPERT.

The registrant's Board of Trustees has determined that it has at least one audit committee financial expert serving on its audit committee (the "Audit Committee"), Ronald E. Toupin, Jr. Mr. Toupin is an "independent" Trustee for purposes of this Item 3 of Form N-CSR. Mr. Toupin qualifies as an audit committee financial expert by virtue of his experience obtained as a portfolio manager and research analyst, which included review and analysis of offering documents and audited and unaudited financial statements using GAAP to show accounting estimates, accruals and reserves.

(Under applicable securities laws, a person who is determined to be an audit committee financial expert will not be deemed an "expert" for any purpose, including without limitation for the purposes of Section 11 of the Securities Act of 1933, as amended, as a result of being designated or identified as an audit committee financial expert. The designation or identification of a person as an audit committee financial expert does not impose on such person any duties, obligations, or liabilities that are greater than the duties, obligations, and liabilities imposed on such person as a member of the Audit Committee and Board of Trustees in the absence of such designation or identification. The designation of identification of a person as an audit committee financial expert does not affect the duties, obligations or liability of any other member of the Audit Committee or Board of Trustees.)

ITEM 4. PRINCIPAL ACCOUNTANT FEES AND SERVICES.

(a) Audit Fees: the aggregate fees billed for professional services rendered by the principal accountant for the audit of the registrant's annual financial statements or services that are normally provided by the accountant in connection with statutory and regulatory filings or engagements were $41,500 and $40,000 for the fiscal years ending December 31, 2008, and December 31, 2007, respectively.

(b) Audit-Related Fees: the aggregate fees billed for assurance and related services by the principal accountant that are reasonably related to the performance of the audit of the registrant's financial statements and are not reported under paragraph (a) of this Item were $0 and $0 for the fiscal years ending December 31, 2008, and December 31, 2007, respectively.

(c) Tax Fees: the aggregate fees billed for professional services rendered by the principal accountant for tax compliance, tax advice, and tax planning, were $6,500 and $6,200 for the fiscal years ending December 31, 2008 and December 31, 2007, respectively.

(d) All Other Fees: the aggregate fees billed for products and services provided by the principal accountant, other than the services reported in paragraphs (a) through (c) of this Item were $0 and $0 for the fiscal years ending December 31, 2008, and December 31, 2007, respectively.

The registrant's principal accountant did not bill fees for non-audit services that required approval by the Audit Committee pursuant to paragraph (c)(7)(ii) of Rule 2-01 of Regulation S-X during the Registrant's last two fiscal years.

(e). Audit Committee Pre-Approval Policies and Procedures.

(i) The Audit Committee reviews, and in its sole discretion, pre-approves, pursuant to written pre-approval procedures (A) all engagements for audit and non-audit services to be provided by the principal accountant to the registrant and (B) all engagements for non-audit services to be provided by the principal accountant (1) to the registrant's investment adviser (not including a sub-adviser whose role is primarily portfolio management and is sub-contracted or overseen by another investment adviser) and (2) to any entity controlling, controlled by or under common control with the registrant's investment adviser that provides ongoing services to the registrant; but in the case of the services described in subsection (B)(1) or (2), only if the engagement relates directly to the operations and financial reporting of the registrant; provided that such pre-approval need not be obtained in circumstances in which the pre-approval requirement is waived under rules promulgated by the Securities and Exchange Commission or New York Stock Exchange listing standards. Sections
IV.C.2 and IV.C.3 of the Audit Committee's revised Audit Committee Charter contain the Audit Committee's Pre-Approval Policies and Procedures and such sections are included below.

IV.C.2 Pre-approve any engagement of the independent auditors to provide any non-prohibited services to the Fund, including the fees and other compensation to be paid to the independent auditors (unless an exception is available under Rule 2-01 of Regulation S-X).

(a) The Chairman or any member of the Audit Committee may grant the pre-approval of services to the Fund for non-prohibited services up to $10,000. All such delegated pre-approvals shall be presented to the Audit Committee no later than the next Audit Committee meeting.

IV.C.3 Pre-approve any engagement of the independent auditors, including the fees and other compensation to be paid to the independent auditors, to provide any non-audit services to the Adviser (or any "control affiliate" of the Adviser providing ongoing services to the Fund), if the engagement relates directly to the operations and financial reporting of the Fund (unless an exception is available under Rule 2-01 of Regulation S-X).

(a) The Chairman or any member of the Audit Committee may grant the pre-approval for non-audit services to the Adviser up to $10,000. All such delegated pre-approvals shall be presented to the Audit Committee no later than the next Audit Committee meeting.

(ii) None of the services described in each of Items 4(b) through (d) were approved by the Audit Committee pursuant to paragraph (c)(7)(i)(C) of Rule 2-01 of Regulation S-X.

(f) Not applicable.

(g) The aggregate non-audit fees billed by the registrant's accountant for services rendered to the registrant, the registrant's investment adviser (not including a sub-adviser whose role is primarily portfolio management and is sub-contracted with or overseen by another investment adviser) and any entity controlling, controlled by, or under common control with the adviser that provides ongoing services to the registrant that directly related to the operations and financial reporting of the registrant was $6,500 and $6,200 for the fiscal years ending December 31, 2008, and December 31, 2007, respectively.

(h) Not applicable.

ITEM 5. AUDIT COMMITTEE OF LISTED REGISTRANTS.

(a) The Audit Committee was established in accordance with Section 3(a)(58)(A) of the Securities Exchange Act of 1934, as amended. The audit committee of the registrant is composed of: Randall C. Barnes, Steven D. Cosler, Robert M. Hamje, L. Kent Moore, Ronald A. Nyberg and Ronald E. Toupin, Jr.

(b) Not Applicable.

ITEM 6. SCHEDULE OF INVESTMENTS.

The Schedule of Investments is included as part of Item 1.

ITEM 7. DISCLOSURE OF PROXY VOTING POLICIES AND PROCEDURES FOR CLOSED-END MANAGEMENT INVESTMENT COMPANIES.

The registrant has delegated the voting of proxies relating to its voting securities to its investment sub-adviser, Analytic Investors, LLC (the "Sub-Adviser" or "Analytic"). The Sub-Adviser's proxy voting policies and procedures are included as an exhibit hereto.

ITEM 8. PORTFOLIO MANAGERS OF CLOSED-END MANAGEMENT INVESTMENT COMPANIES.

A team of investment professionals at Analytic shares primary responsibility for the day-to-day portfolio management of the Fund. Mr. McMurran and Mr. Bein oversee the team regarding the management of the Fund. The following provides information regarding the members of the team.

NAME SINCE PROFESSIONAL EXPERIENCE
---- ----------- -----------------------
Gregory M. McMurran 2005 Mr. McMurran (Chief Investment
 (Inception) Officer and Portfolio Manager) is
 responsible for the management of
 implementation of Analytic's
 investment strategies, including
 those used for the Fund. He joined
 Analytic in 1976. He is a major
 contributor to the firm's ongoing
 research efforts as well as new
 product development and strategy
 applications. Mr. McMurran has an
 extensive background in the
 implementation of the firm's
 quantitative investment strategies.
 He received a B.S. in Economics from
 the University of California,
 Irvine. He also received an M.A. in
 Economics at California State
 University, Fullerton. He has 31
 years of industry experience.

Harindra de Silva, 2005 Dr. de Silva (President and
Ph.D., CFA (Inception) Portfolio Manager) is responsible
 for Analytic's strategic direction
 and the ongoing development of its
 investment processes. He focuses on
 the ongoing research and portfolio
 management efforts for the firm's
 U.S. equity strategies and Tactical
 Asset Allocation strategies. Before
 joining Analytic in 1995, he was a
 principal at Analysis Group, Inc.,
 where he was responsible for
 providing economic research services
 to institutional investors including
 investment managers, large pension
 funds and endowments. He received a
 Ph.D. in Finance from the University
 of California, Irvine. He holds a
 B.S. in Mechanical Engineering from
 the University of Manchester
 Institute of Science and Technology
 and an M.B.A. in Finance and an M.S.
 in Economic Forecasting from the
 University of Rochester. Dr. de
 Silva is a member of the Association
 for Investment Management and
 Research, the American Finance
 Association and the International
 Association of Financial Analysts.
 He has 23 years of industry
 experience.

Dennis Bein, CFA 2005 Mr. Bein (Chief Investment Officer
 (Inception) and Portfolio Manager) is
 responsible for the ongoing research
 for Analytic's U.S. equity
 strategies as well as the day-to-day
 portfolio management and trading of
 those accounts. Before joining
 Analytic in 1995, Mr. Bein was a
 Senior Consultant for AG Risk
 Management, Analysis Group, Inc.'s
 investment consulting subsidiary. He
 received an M.B.A. from the Anderson
 Graduate School of Management at the
 University of California, Riverside.
 Mr. Bein completed his undergraduate
 studies in Business Administration
 at the University of California,
 Riverside. He is a Chartered
 Financial Analyst and a member of
 the Association for Investment
 Management and Research, the
 Institute of Chartered Financial
 Analysts and the Los Angeles Society
 of Financial Analysts. He has 18
 years of industry experience.

Yigal Newman, Ph.D 2009 Dr. Newman (Portfolio Manager) is
 responsible for ongoing research and
 development of options and other
 volatility based-investment
 strategies as well as the day-to-day
 portfolio management and trading of
 such accounts. Before joining
 Analytic in 2005, he was previously
 employed at Dimensional Fund
 Advisors (DFA) where he worked on
 various alpha generation and
 quantitative analysis projects. Dr.
 Newman received a Ph.D in Finance
 from the Graduate School of Business
 at Stanford University and a B.S. in
 Industrial Engineering and
 Management from the Israel Institute
 of Technology.

Ram Willner, D.B.A 2009 Mr. Willner (Portfolio Manager) is
 responsible for the ongoing research
 and development of fixed income and
 currency based strategies as well as
 the day-to-day portfolio management
 and trading of such accounts. Before
 joining Analytic in 2008, Mr.
 Willner led global analytics at
 PIMCO and Banc of America Capital
 Management (BACAP) Fixed Income
 Department. For the past 10 years,
 Ram extended his quantitative
 background to serve as a domestic
 and international fixed income
 portfolio manager, managing real
 money and levered investments at
 Morgan Stanley Asset Management (in
 London), at BACAP, and at Global
 Fixed Income Partners. Ram has
 lectured and published extensively
 on fixed income topics, particularly
 with an emphasis on quantitative
 approaches. Mr. Willner received a
 D.B.A. in Financial Mathematics from
 Harvard University; an MBA from
 Carnegie Mellon University; and a
 B.A. in Mathematics with Honors from
 Brandeis University. He has 21 years
 of industry experience.

Steven Sapra, CFA 2005 Mr. Sapra (Portfolio Manager) is
 (Inception) responsible for the ongoing research
 for Analytic's U.S. equity
 strategies as well as day-to-day
 portfolio management and trading.
 Before joining Analytic in 1999, Mr.
 Sapra was a Senior Consultant for
 BARRA, Inc. He received an M.A. in
 Economics from the University of
 Southern California and a B.S. in
 Economics from California State
 Polytechnic University, Pomona. He
 is a Chartered Financial Analyst and
 a member of the CFA Institute and
 the Los Angeles Society of Financial
 Analysts. He has 11 years of
 industry experience.

David Krider, CFA 2005 Mr. Krider (Portfolio Manager) is
 (Inception) responsible for the ongoing research
 and development of global equity
 based investment strategies as well
 as the day-to-day trading of global
 portfolios. Before joining Analytic
 in 2005, Mr. Krider was founder and
 Chief Technology Officer of
 Visualize, Inc., a firm that
 specializes in financial
 visualization and analytic software.
 He was also a research associate at
 First Quadrant before leaving to
 start his own firm. He received a
 B.S. in Economics and Computer
 Science from California Institute of
 Technology.

Gregory McMurran and Dennis Bein, as Analytic Chief Investment Officers, generally oversee all aspects of the day-to-day management of the Fund. Mr. McMurran has primary responsibility for the oversight of the firm's derivatives based investment strategies and Mr. Bein has primary responsibility for the oversight of the firm's equity based investment strategies. Under Mr. McMurran's direction, Ram Willner and David Krider serve as portfolio managers for global asset allocation strategies and Yigal Newman serves as lead portfolio manager for options and other volatility based strategies. Under Mr. Bein's direction, Steven Sapra serves as lead portfolio manager for U.S. equity based strategies, and Harindra de Silva heads the firm's research efforts on behalf of the Fund.

The following summarizes the structure of and methods used to determine the compensation of each individual, each of whom is employed by the Sub-Adviser, that shares primary responsibility for the day-to-day portfolio management of the Fund (the "Analytic Portfolio Managers"):

Compensation. Analytic's compensation structure for professional employees consists of an industry median base salary (based on independent industry information) and an annual discretionary bonus. Bonus amounts are determined using the following factors: the overall success of the firm in terms of profitability; the overall success of the department or team; and an individual's contribution to the team based on goals established during the performance period. In October 2007, the Analytic board adopted an equity plan that allows key employees of the firm to hold up to 24.9% direct or indirect nonvoting equity interests in the firm. Old Mutual will maintain its majority ownership in the firm. Participants in the Analytic Investors LLC Equity Plan include our executive management team and senior investment team members.

The base salaries of the Analytic Portfolio Managers are typically reviewed on an annual basis, determined by each portfolio manager's date of employment. Discretionary bonuses are determined annually, based upon an analysis of information from the prior calendar year. Profit sharing allocations are made on an annual basis.

Conflicts of Interest. Analytic and its officers, employees and beneficial owners shall be free from time to time to acquire, possess, manage, and dispose of securities or other investment assets for their own accounts, for the accounts of their families, for the account of any entity in which they have a beneficial interest or for the accounts of others for whom they may provide investment advisory, brokerage or other services (collectively, "Managed Accounts"), in transactions which may or may not correspond with transactions effected or positions held in the Fund. It is understood that when Analytic determines that it would be appropriate for the Fund and one or more Managed Accounts to participate in an investment opportunity, Analytic will seek to execute orders for the Fund and for such Managed Accounts on a basis which it considers equitable, but that equality of treatment of the Fund and other Managed Accounts is not assured. In such situations, Analytic may (but is not be required to) place orders for the Fund and each other Managed Account simultaneously and if all such orders are not filled at the same price, Analytic may cause the Fund and each Managed Account to pay or receive the average of the prices at which the orders were filled. If all such orders cannot be fully executed under prevailing market conditions, Analytic may allocate the securities traded among the Fund and other Managed Accounts in a manner which it considers equitable, taking into account the size of the order placed for the Fund and each other Managed Account as well as any other factors which it deems relevant.

Certain of the Managed Accounts Analytic advises may sell securities short, including securities with respect to which other Managed Accounts hold long positions. The portfolio managers and traders for these Managed Accounts are not separated from the rest of Analytic's investment personnel and therefore have access to full information about Analytic's investment research and the investment decisions and strategies being employed for the Managed Accounts. These Managed Accounts pay Analytic management fees at rates comparable to and in some cases lower than those paid by the Fund and other Managed Accounts. Analytic also receives a significant

share of any profits earned by certain of the Managed Accounts as incentive compensation. As a result, Analytic may have a conflict between its own interests and the interests of other Analytic investment advisory clients in managing the portfolios of certain of these Managed Accounts.

In order to minimize these potential conflicts of interest, Analytic has adopted various procedures and safeguards. For example, except for short sales done to take advantage of short-term volatility, Analytic will not sell a security short that another Managed Account owns until (1) it discloses to the relevant portfolio managers its intention to sell short and the reasons for selling short and (2) allows the portfolio managers a reasonable time to make an investment decision to hold or sell that security.

Other accounts managed. The following summarizes information regarding each of the other accounts managed by the Analytic Portfolio Managers as of December 31, 2008:

 REGISTERED INVESTMENT OTHER POOLED
 COMPANIES INVESTMENT VEHICLES OTHER ACCOUNTS
 -------------------------- ----------------------------- ----------------------------
 # OF TOTAL ASSETS # OF TOTAL ASSETS # OF TOTAL ASSETS
NAME ACCOUNTS ($MILLION) ACCOUNTS ($MILLION) ACCOUNTS ($MILLION)
---- -------- ------------ -------- ------------ -------- ------------
Dennis Bein 13 (0) $3,097.6 22 (12) $2,485.1 35 (13) $2,387.3
 ($0) ($1,608.1) ($947.4)

Harindra de Silva 14 (0) $3,207.8 21 (12) $1,830.3 33 (13) $2,497.3
 ($0) ($901.6) ($947.4)

David Krider 3 (0) $293.0 ($0) 3 (0) $160.5 ($0) 2 (2) $277.3
 ($277.3)

Greg McMurran 6 (0) $678.1 ($0) 2 (1) $117.5 ($8.4) 3 (0) $179.7 ($0)

Yigal Newman 0 (0) $0 ($0) 0 (0) $0 ($0) 0 (0) $0 ($0)

Steven Sapra 10 (0) $2,804.6 13 (7) $1,745.9 30 (8) $2,035.9
 ($0) ($1,133.3) ($596.1)

Ram Willner 1 (0) $56.6 ($0) 0 (0) $0 ($0) 1 (0) $13.6 ($0)

( ) represents the number and value of accounts within the total accounts that are subject to a performance based advisory fee.

Securities ownership. The following table discloses the dollar range of equity securities of the Fund beneficially owned by the each of the Analytic Portfolio Managers as of December 31, 2008:

 DOLLAR RANGE OF EQUITY
NAME OF PORTFOLIO MANAGER SECURITIES IN FUND
--------------------------------------------------------------------------------
Dennis Bein None
Harindra de Silva None
David Krider None
Greg McMurran None
Yigal Newman None
Steven Sapra None
Ram Willner None

ITEM 9. PURCHASES OF EQUITY SECURITIES BY CLOSED-END MANAGEMENT INVESTMENT COMPANY AND AFFILIATED PURCHASERS.

None.

ITEM 10. SUBMISSION OF MATTERS TO A VOTE OF SECURITY HOLDERS.

On January 20, 2009, the registrant's Board of Trustees (the "Board") approved a revised written charter (the "Nominating and Governance Charter") for its nominating and governance committee (the "Nominating and Governance Committee") that contains changes to the procedures by which shareholders may recommend nominees to the Board.

Under the Nominating and Governance Charter, the previously existing procedures by which shareholders may recommend nominees to the Board remain in effect. In addition to these previously existing procedures, the Nominating and Governance Charter includes a new requirement that following the submission by a shareholder of a Trustee candidate recommendation, such Trustee candidate must
(i) be prepared to submit written answers to a questionnaire seeking professional and personal information that will assist the Nominating and Governance Committee to evaluate the candidate and to determine, among other matters, whether the candidate would qualify as a Trustee who is not an "interested person" of the registrant as such term is defined under the Investment Company Act of 1940; (ii) be prepared to submit character references and agree to appropriate background checks; and (iii) be prepared to meet with one or more members of the Nominating and Governance Committee at a time and location convenient to those Nominating and Governance Committee members in order to discuss the nominee's qualifications.

A copy of the Nominating and Governance Committee Charter will be filed with the Securities and Exchange Commission as an appendix to the registrant's 2009 annual shareholder meeting proxy statement.

ITEM 11. CONTROLS AND PROCEDURES.

(a) The registrant's principal executive officer and principal financial officer have evaluated the registrant's disclosure controls and procedures (as defined in Rule 30a3(c) under the Investment Company Act of 1940) as of a date within 90 days of this filing and have concluded based on such evaluation as required by Rule 30a-3(b) under the Investment Company Act of 1940, that the registrant's disclosure controls and procedures were effective, as of that date, in ensuring that information required to be disclosed by the registrant in this Form N-CSR was recorded, processed, summarized, and reported within the time periods specified in the Securities and Exchange Commission's rules and forms.

(b) There were no changes in the registrant's internal control over financial reporting (as defined in Rule 30a-3(d) under the Investment Company Act of 1940) that occurred during the registrant's second fiscal quarter of the period covered by this report that have materially affected, or are reasonably likely to materially affect, the registrant's internal control over financial reporting.

ITEM 12. EXHIBITS.

(a) (1) Code of Ethics for Chief Executive and Senior Officers.

(a) (2) Certifications of principal executive officer and principal financial officer pursuant to Rule 30a-2(a) of the Investment Company Act of 1940.

(a) (3) Not Applicable.

(b) Certifications of principal executive officer and principal financial officer pursuant to Rule 30a-2(b) of the Investment Company Act of 1940 and
Section 906 of the Sarbanes-Oxley Act of 2002.

(c) Proxy Voting Policies and Procedures.

SIGNATURES

Pursuant to the requirements of the Securities Exchange Act of 1934 and the Investment Company Act of 1940, the registrant has duly caused this report to be signed on its behalf by the undersigned, thereunto duly authorized.

(Registrant) Old Mutual/Claymore Long-Short Fund

By: /s/ J. Thomas Futrell
 ------------------------------------------------------------------

Name: J. Thomas Futrell

Title: Chief Executive Officer

Date: March 5, 2009

Pursuant to the requirements of the Securities Exchange Act of 1934 and the Investment Company Act of 1940, this report has been signed by the following persons on behalf of the registrant and in the capacities and on the dates indicated.

By: /s/ J. Thomas Futrell
 ------------------------------------------------------------------

Name: J. Thomas Futrell

Title: Chief Executive Officer

Date: March 5, 2009

By: /s/ Steven M. Hill
 ------------------------------------------------------------------

Name: Steven M. Hill

Title: Chief Financial Officer, Chief Accounting Officer and Treasurer

Date: March 5, 2009

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