FORM 4
[ ] Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).         
UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP OF SECURITIES
                                                                                  
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Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934 or Section 30(h) of the Investment Company Act of 1940
                      

1. Name and Address of Reporting Person *

K2 PRINCIPAL FUND, L.P.
2. Issuer Name and Ticker or Trading Symbol

SIMPLICITY ESPORTS & GAMING Co [ WINR ]
5. Relationship of Reporting Person(s) to Issuer (Check all applicable)

_____ Director                      __ X __ 10% Owner
_____ Officer (give title below)      _____ Other (specify below)
(Last)          (First)          (Middle)

2 BLOOR STREET WEST, SUITE 801
3. Date of Earliest Transaction (MM/DD/YYYY)

1/9/2019
(Street)

TORONTO, A6 M4W 3E2
(City)        (State)        (Zip)
4. If Amendment, Date Original Filed (MM/DD/YYYY)

 
6. Individual or Joint/Group Filing (Check Applicable Line)

___ Form filed by One Reporting Person
_ X _ Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1.Title of Security
(Instr. 3)
2. Trans. Date 2A. Deemed Execution Date, if any 3. Trans. Code
(Instr. 8)
4. Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5)
5. Amount of Securities Beneficially Owned Following Reported Transaction(s)
(Instr. 3 and 4)
6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V Amount (A) or (D) Price

Table II - Derivative Securities Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities)
1. Title of Derivate Security
(Instr. 3)
2. Conversion or Exercise Price of Derivative Security 3. Trans. Date 3A. Deemed Execution Date, if any 4. Trans. Code
(Instr. 8)
5. Number of Derivative Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5)
6. Date Exercisable and Expiration Date 7. Title and Amount of Securities Underlying Derivative Security
(Instr. 3 and 4)
8. Price of Derivative Security
(Instr. 5)
9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares
Forward Sale Agreement (obligation to sell)     (1) 1/9/2019     S         700    1/18/2019   1/18/2019   Common Stock   700   $3.31   192716   D    
Forward Sale Agreement (obligation to sell)     (1) 1/10/2019     S         62494    1/18/2019   1/18/2019   Common Stock   62494   $4.5564   130222   D    
Warrant   $11.5   1/9/2019     S         13489    11/23/2018   5/22/2024   Common Stock   13489   $0.3754   781655   D    

Explanation of Responses:
(1)  Pursuant to a forward sale agreement between the Reporting Person and the issuer, as amended, the Reporting Person will be obligated to sell 220,000 shares (the "Original Shares") to the issuer on behalf of K2 on January 18, 2019 unless such Original Shares are sold by the Reporting Person prior to such date. The prices at which the Reporting Person will be obligated to sell any remaining shares of the Original Shares to the issuer on January 18, 2019 are as follows: (i) first, $6.00 per remaining share up to 20% of the Original Shares; (ii) then, $5.00 per remaining share up to 20% of the Original Shares; (iii) then, $4.00 per remaining share up to 20% of the Original Shares; (iv) then, $3.00 per remaining share up to 20% of the Original Shares; and (v) then, $2.00 per remaining share up to 20% of the Original Shares.

Reporting Owners
Reporting Owner Name / Address
Relationships
Director 10% Owner Officer Other
K2 PRINCIPAL FUND, L.P.
2 BLOOR STREET WEST
SUITE 801
TORONTO, A6 M4W 3E2

X

K2 GENPAR LP
2 BLOOR STREET WEST
SUITE 801
TORONTO, A6 M4W 3E2

X

K2 GENPAR 2009 INC
2 BLOOR STREET WEST
SUITE 801
TORONTO, A6 M4W 3E2

X

Shawn Kimel Investments, Inc.
2 BLOOR STREET WEST
SUITE 801
TORONTO, A6 M4W 3E2

X

K2 & Associates Investment Management Inc.
2 BLOOR STREET WEST
SUITE 801
TORONTO, A6 M4W 3E2

X

Kimel Shawn
2 BLOOR STREET WEST
SUITE 801
TORONTO, A6 M4W 3E2

X


Signatures
/s/ Daniel Gosselin, President, The K2 Principal Fund L.P. 1/10/2019
** Signature of Reporting Person Date

/s/ Daniel Gosselin, President, K2 Genpar L.P 1/10/2019
** Signature of Reporting Person Date

/s/ Daniel Gosselin, President, K2 Genpar 2009 Inc. 1/10/2019
** Signature of Reporting Person Date

/s/ Daniel Gosselin, President, Shawl Kimel Investments Inc. 1/10/2019
** Signature of Reporting Person Date

/s/ Daniel Gosselin, President, K2 & Associates Investment Management Inc. 1/10/2019
** Signature of Reporting Person Date

/s/ Daniel Gosselin, in his individual capacity 1/10/2019
** Signature of Reporting Person Date


Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4(b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB control number.
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