| 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 | ||||
| 6. Round | 29/03/2025 | Inter Miami CF | - | Philadelphia Union | 2:1 | ||||
| 7. Round | 06/04/2025 | Philadelphia Union | - | Orlando City | 0:0 | ||||
| 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 | ||||
| 16. Round | 29/05/2025 | Toronto FC | - | Philadelphia Union | 1:2 |
Jamaica
USA 