| 1. Round | 23/02/2025 | Columbus Crew | - | Chicago Fire | 4:2 | ||||
| 2. Round | 02/03/2025 | Chicago Fire | - | D.C. United | 2:2 | ||||
| 3. Round | 09/03/2025 | FC Dallas | - | Chicago Fire | 1:3 | ||||
| 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 |  |
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| 10. Round | 27/04/2025 | Nashville SC | - | Chicago Fire | 7:2 | ||||
| 17. Round | 01/06/2025 | Orlando City | - | Chicago Fire | 1:3 | ||||
| 18. Round | 08/06/2025 | D.C. United | - | Chicago Fire | 1:7 | |
USA