| 2. Round | 19/07/2020 | Philadelphia Union 2 | - | Pittsburgh Riverhounds | 0:6 | ||||
| 2. Round | 26/07/2020 | Hartford Athletic | - | Philadelphia Union 2 | 3:2 | ||||
| 3. Round | 02/08/2020 | Pittsburgh Riverhounds | - | Philadelphia Union 2 | 4:0 | ||||
| 4. Round | 03/09/2020 | Philadelphia Union 2 | - | Atlanta United II | 1:2 | ||||
| 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 | 26/09/2020 | New York RB II | - | Philadelphia Union 2 | 5:4 |  |
Jamaica