Company: GAME
Filing Date: 2025-10-06
Form Type: DEFA14A
Source: 0001493152-25-017029
Chunk: 1

Company: GameSquare Holdings, Inc.
Filing Date: 2025-10-06
Form: DEFA14A
Chunk 1
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 key statutory merger with a wholly-owned subsidiary. I want to stress that the statutory merger vote is technical in nature, but it is essential.

Approving this proposal allows GameSquare to:

| ● | modernize                                                                           
 and simplify our governing documents,                                               |
| ● | provide                                                                             
 strategic flexibility to support future growth and capital markets initiatives, and |
| ● | align                                                                               
 our governance framework with best-in-class market practices.                       |

Let me be clear: your vote matters. Regardless of the size of your holdings, your proxy is powerful. Without broad support, we risk stalling our transformation. Do not allow inertia to undermine the progress we have worked so hard to build.

Shareholders who have any questions or require assistance with voting may contact the Company’s proxy solicitation agent and shareholder communications advisor:

Laurel Hill Advisory Group

Toll Free (North America): 1-888.742.1305

International: +1-416-304-0211

By Email: Jdepinto@laurelhill.com

Strategic Progress Acquisition of Click Management & Operational Optimization

Since that call to action, we have continued executing with discipline and purpose. On September 11, 2025, GameSquare announced the acquisition of Click Management, a high-performing talent agency, with the expectation that this move will be accretive to profitability in 2025.

Key Highlights of the Click Acquisition:

| ● | Click                                                                                                    
 Management generated $12.4 million in revenue in 2024 and has closed over 545 commercial deals globally. |

| ● | We                                                                                                                                
 expect, in the second half of 2025, Click will contribute $14.5 million annualized of pro-forma revenue and about $1.2 million of 
 annualized pro-forma EBITDA, before we realize any operating synergies.                                                           |

GameSquare’s Strong Financial and Operating Position Driving Positive Momentum

| ● | On                                                                                                                                 
 a pro forma basis, we expect $36.8 million in revenue and $2.9 million in adjusted EBITDA for the second half of 2025.             |
| ● | As                                                                                                                                 
 of August 31, 2025, we held $87.7 million in cash and on-chain holdings, with less than $2 million of debt outstanding.            |
| ● | We                                                                                                                                 
 have divested Frankly Media, a low-margin operation that despite having revenue of $46.9 million in 2024, contributed to an EBITDA