| 3. Round | 03/08/2020 | Hartford Athletic | - | Loudoun United | 4:1 | ||||
| 3. Round | 13/08/2020 | New York RB II | - | Loudoun United | 1:2 |  |
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| 3. Round | 16/08/2020 | Louisville City FC | - | Loudoun United | 2:0 | ||||
| 3. Round | 20/08/2020 | Loudoun United | - | Pittsburgh Riverhounds | 0:2 | ||||
| 3. Round | 24/08/2020 | Hartford Athletic | - | Loudoun United | 2:2 | ||||
| 3. Round | 29/08/2020 | Loudoun United | - | New York RB II | 2:3 | ||||
| 4. Round | 02/09/2020 | Pittsburgh Riverhounds | - | Loudoun United | 3:0 | ||||
| 4. Round | 06/09/2020 | Hartford Athletic | - | Loudoun United | 2:1 |  |
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| 4. Round | 17/09/2020 | Philadelphia Union 2 | - | Loudoun United | 4:0 | ||||
| 4. Round | 19/09/2020 | Loudoun United | - | Pittsburgh Riverhounds | 0:1 |
USA