| 1. Round | 08/03/2020 | Philadelphia Union 2 | - | Loudoun United | 0:0 | ||||
| 4. Round | 09/09/2020 | New York RB II | - | Philadelphia Union 2 | 6:0 |  |
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| 4. Round | 13/09/2020 | Loudoun United | - | Philadelphia Union 2 | 1:1 | ||||
| 4. Round | 17/09/2020 | Philadelphia Union 2 | - | Loudoun United | 4:0 | ||||
| 4. Round | 20/09/2020 | Hartford Athletic | - | Philadelphia Union 2 | 3:0 | ||||
| 4. Round | 24/09/2020 | Philadelphia Union 2 | - | Hartford Athletic | 1:1 | ||||
| 4. Round | 26/09/2020 | New York RB II | - | Philadelphia Union 2 | 5:4 |
USA
Germany