| 2. Round | 03/05/2021 | Miami FC | - | Loudoun United | 2:1 | ||||
| 2. Round | 19/05/2021 | Loudoun United | - | New York RB II | 1:2 |  |
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| 2. Round | 30/05/2021 | New Mexico United | - | Loudoun United | 0:1 | ||||
| 3. Round | 03/06/2021 | Loudoun United | - | Pittsburgh Riverhounds | 2:3 |  |
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| 3. Round | 09/06/2021 | Loudoun United | - | Charleston Battery | 0:1 | ||||
| 3. Round | 12/06/2021 | Tampa Bay Rowdies | - | Loudoun United | 2:1 | ||||
| 3. Round | 01/07/2021 | Loudoun United | - | Pittsburgh Riverhounds | 2:1 |
USA