| 4. Round | 10/06/2023 | Loudoun United | - | FC Tulsa | 3:1 | ||||
| 4. Round | 18/06/2023 | Miami FC | - | Loudoun United | 1:2 | ||||
| 4. Round | 22/06/2023 | Birmingham Legion | - | Loudoun United | 2:0 | ||||
| 4. Round | 25/06/2023 | Loudoun United | - | Tampa Bay Rowdies | 2:4 | ||||
| 5. Round | 01/07/2023 | Charleston Battery | - | Loudoun United | 3:0 |  |
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| 5. Round | 09/07/2023 | Louisville City FC | - | Loudoun United | 1:0 | ||||
| 5. Round | 13/07/2023 | Detroit City FC | - | Loudoun United | 1:1 | ||||
| 5. Round | 30/07/2023 | Loudoun United | - | Miami FC | 1:2 | ||||
| 6. Round | 02/08/2023 | Loudoun United | - | Memphis 901 | 0:0 | ||||
| 6. Round | 13/08/2023 | Las Vegas Lights FC | - | Loudoun United | 0:3 |  |
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| 6. Round | 20/08/2023 | Loudoun United | - | Sacramento Republic | 1:3 | ||||
| 6. Round | 27/08/2023 | Indy Eleven | - | Loudoun United | 2:1 | ||||
| 7. Round | 23/09/2023 | Loudoun United | - | Louisville City FC | 1:2 | ||||
| 8. Round | 15/10/2023 | Rio Grande Valley FC | - | Loudoun United | 2:1 |
USA