6. Round | 27/08/2023 | Indy Eleven | - | Loudoun United | 2:1 | ||||
7. Round | 10/09/2023 | Pittsburgh Riverhounds | - | Loudoun United | 3:1 | ||||
7. Round | 17/09/2023 | Loudoun United | - | Charleston Battery | 2:2 | ||||
7. Round | 23/09/2023 | Loudoun United | - | Louisville City FC | 1:2 | ||||
7. Round | 01/10/2023 | Tampa Bay Rowdies | - | Loudoun United | 1:0 | ||||
8. Round | 07/10/2023 | Loudoun United | - | Detroit City FC | 0:3 | ||||
8. Round | 15/10/2023 | Rio Grande Valley FC | - | Loudoun United | 2:1 |