| 3. Round | 02/08/2020 | Pittsburgh Riverhounds | - | Philadelphia Union 2 | 4:0 | ||||
| 3. Round | 05/08/2020 | Philadelphia Union 2 | - | New York RB II | 3:2 |  |
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| 4. Round | 03/09/2020 | Philadelphia Union 2 | - | Atlanta United II | 1:2 | ||||
| 4. Round | 07/09/2020 | Tampa Bay Rowdies | - | Philadelphia Union 2 | 2:0 | ||||
| 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 | |
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| 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 | ||||
| 5. Round | 01/10/2020 | Philadelphia Union 2 | - | Hartford Athletic | 2:3 | ||||
| 5. Round | 04/10/2020 | Pittsburgh Riverhounds | - | Philadelphia Union 2 | 2:1 |
Ivory Coast