| 3. Round | 09/04/2023 | Chicago Fire | - | Minnesota United FC | 2:1 |  |
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| 4. Round | 07/05/2023 | Nashville SC | - | Chicago Fire | 3:0 | |
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| 4. Round | 28/05/2023 | New England Revolution | - | Chicago Fire | 3:3 | ||||
| 5. Round | 04/06/2023 | FC Cincinnati | - | Chicago Fire | 1:0 | ||||
| 5. Round | 22/06/2023 | Portland Timbers | - | Chicago Fire | 1:2 | ||||
| 6. Round | 02/07/2023 | Orlando City | - | Chicago Fire | 3:1 | ||||
| 8. Round | 21/09/2023 | Columbus Crew | - | Chicago Fire | 3:0 | ||||
| 8. Round | 24/09/2023 | Chicago Fire | - | New England Revolution | 2:2 | ||||
| 8. Round | 01/10/2023 | New York RB | - | Chicago Fire | 0:1 | ||||
| 9. Round | 05/10/2023 | Chicago Fire | - | Inter Miami CF | 4:1 | ||||
| 9. Round | 08/10/2023 | Chicago Fire | - | Charlotte FC | 0:2 |
USA