| 2. Round | 19/05/2021 | Loudoun United | - | New York RB II | 1:2 | ||||
| 3. Round | 20/06/2021 | Hartford Athletic | - | Loudoun United | 2:1 | ||||
| 3. Round | 27/06/2021 | Charleston Battery | - | Loudoun United | 3:0 | ||||
| 4. Round | 04/07/2021 | Loudoun United | - | Hartford Athletic | 0:2 | ||||
| 4. Round | 11/07/2021 | Loudoun United | - | Miami FC | 1:4 |  |
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| 4. Round | 25/07/2021 | Tampa Bay Rowdies | - | Loudoun United | 3:1 | ||||
| 4. Round | 28/07/2021 | Loudoun United | - | Charleston Battery | 3:5 | |
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| 5. Round | 14/08/2021 | Charleston Battery | - | Loudoun United | 1:0 |
USA