| 1. Round | 23/02/2025 | Columbus Crew | - | Chicago Fire | 4:2 |  |
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| 2. Round | 02/03/2025 | Chicago Fire | - | D.C. United | 2:2 | ||||
| 4. Round | 15/03/2025 | Toronto FC | - | Chicago Fire | 1:2 | ||||
| 5. Round | 23/03/2025 | Vancouver Whitecaps | - | Chicago Fire | 1:3 |  |
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| 6. Round | 30/03/2025 | Chicago Fire | - | CF Montréal | 1:1 | |
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| 7. Round | 06/04/2025 | New York RB | - | Chicago Fire | 2:1 | ||||
| 8. Round | 13/04/2025 | Chicago Fire | - | Inter Miami CF | 0:0 | ||||
| 9. Round | 20/04/2025 | Chicago Fire | - | FC Cincinnati | 2:3 |
Denmark