Company: GAME
Filing Date: 2025-10-09
Form Type: DEFA14A
Source: 0001493152-25-017539
Chunk: 0

Company: GameSquare Holdings, Inc.
Filing Date: 2025-10-09
Form: DEFA14A
Chunk 0
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<div align='center'>UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of

the Securities Exchange Act of 1934</div>

| Filed                                
 by the Registrant                    | ☒ |
| Filed                                
 by a Party other than the Registrant | ☐ |

Check the appropriate box:

| ☐ | Preliminary                                                       
 Proxy Statement                                                   |
| ☐ | Confidential,                                                     
 for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) |
| ☐ | Definitive                                                        
 Proxy Statement                                                   |
| ☒ | Definitive                                                        
 Additional Materials                                              |
| ☐ | Soliciting                                                        
 Material under §240.14a-12                                        |

<div align='center'>GAMESQUARE HOLDINGS, INC.

(Name of Registrant as Specified In Its Charter)

Name of Person(s) Filing Proxy Statement, if other than the Registrant</div>

Payment of Filing Fee (Check the appropriate box):

| ☒ | No                                                                                               
 fee required.                                                                                    |
| ☐ | Fee                                                                                              
 paid previously with preliminary materials.                                                      |
| ☐ | Fee                                                                                              
 computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11. |

Explanatory Note: GameSquare Holdings, Inc. (the “Company”) has distributed the following written communication in connection with the Company’s 2025 Annual Meeting of Stockholders. A copy of the written communication can be found below.

Dear Shareholder:

We are reaching out to you regarding GameSquare’s Annual Shareholder Meeting scheduled for November 4, 2025. Shareholders participation in voting is essential for the functioning of corporate governance. Shareholders who owned GameSquare shares on the September 5, 2025, “Record Date” are eligible to vote and we want to ensure your shares are represented at the Meeting. You can vote using the online voting information that you should have received by mail or, if easier, by calling our toll-free voting lineat 888-742-1305(Monday–Friday, 9:00 AM – 5:00 PM EST) to cast your vote directly over the phone.

The GameSquare Board and ISS recommend a vote FOR on all proposals, which can be viewed at: https://www.sec.gov/ix