| 1. Round | 23/02/2025 | Orlando City | - | Philadelphia Union | 2:4 | ||||
| 2. Round | 02/03/2025 | Philadelphia Union | - | FC Cincinnati | 4:1 | ||||
| 3. Round | 09/03/2025 | New England Revolution | - | Philadelphia Union | 0:2 | ||||
| 4. Round | 16/03/2025 | Philadelphia Union | - | Nashville SC | 1:3 |  |
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| 5. Round | 22/03/2025 | Philadelphia Union | - | St. Louis City SC | 1:0 | ||||
| 8. Round | 13/04/2025 | New York City FC | - | Philadelphia Union | 1:0 | ||||
| 9. Round | 20/04/2025 | Philadelphia Union | - | Atlanta United FC | 3:0 | ||||
| 10. Round | 26/04/2025 | Philadelphia Union | - | D.C. United | 3:0 | ||||
| 11. Round | 04/05/2025 | CF Montréal | - | Philadelphia Union | 1:2 | ||||
| 12. Round | 11/05/2025 | Philadelphia Union | - | Columbus Crew | 2:2 | ||||
| 13. Round | 15/05/2025 | Philadelphia Union | - | Los Angeles Galaxy | 3:2 | ||||
| 14. Round | 18/05/2025 | Atlanta United FC | - | Philadelphia Union | 0:1 | |
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| 15. Round | 25/05/2025 | Philadelphia Union | - | Inter Miami CF | 3:3 | ||||
| 16. Round | 29/05/2025 | Toronto FC | - | Philadelphia Union | 1:2 |  |
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| 17. Round | 01/06/2025 | FC Dallas | - | Philadelphia Union | 0:0 |
Germany