| 4. Round | 09/07/2021 | New York RB | - | Philadelphia Union | 1:1 |  |
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| 4. Round | 23/07/2021 | Orlando City | - | Philadelphia Union | 2:1 | ||||
| 4. Round | 26/07/2021 | Inter Miami CF | - | Philadelphia Union | 1:1 | ||||
| 7. Round | 10/10/2021 | FC Cincinnati | - | Philadelphia Union | 1:2 |  |
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| 7. Round | 16/10/2021 | CF Montréal | - | Philadelphia Union | 2:2 | ||||
| 7. Round | 28/10/2021 | Toronto FC | - | Philadelphia Union | 2:2 |
USA
Germany