| 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 | ||||
| 4. Round | 15/03/2025 | Toronto FC | - | Chicago Fire | 1:2 | ||||
| 10. Round | 27/04/2025 | Nashville SC | - | Chicago Fire | 7:2 | ||||
| 11. Round | 04/05/2025 | Chicago Fire | - | Orlando City | 0:0 | ||||
| 12. Round | 10/05/2025 | Chicago Fire | - | Atlanta United FC | 2:1 | ||||
| 14. Round | 18/05/2025 | Charlotte FC | - | Chicago Fire | 1:4 | ||||
| 15. Round | 25/05/2025 | New York City FC | - | Chicago Fire | 3:1 |  |
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| 17. Round | 01/06/2025 | Orlando City | - | Chicago Fire | 1:3 | ||||
| 18. Round | 08/06/2025 | D.C. United | - | Chicago Fire | 1:7 |
USA