| 1. Round | 26/03/2023 | FC Tulsa | - | Loudoun United | 3:0 | ||||
| 2. Round | 01/04/2023 | Loudoun United | - | Colorado Springs Switchbacks | 0:1 | ||||
| 2. Round | 15/04/2023 | Loudoun United | - | Birmingham Legion | 3:0 | ||||
| 2. Round | 23/04/2023 | Loudoun United | - | Oakland Roots | 2:0 | ||||
| 2. Round | 30/04/2023 | Phoenix Rising | - | Loudoun United | 3:1 | ||||
| 3. Round | 28/05/2023 | Loudoun United | - | Pittsburgh Riverhounds | 0:1 | ||||
| 4. Round | 04/06/2023 | Monterey Bay FC | - | Loudoun United | 4:1 |  |
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| 4. Round | 18/06/2023 | Miami FC | - | Loudoun United | 1:2 | ||||
| 4. Round | 25/06/2023 | Loudoun United | - | Tampa Bay Rowdies | 2:4 | ||||
| 5. Round | 16/07/2023 | Loudoun United | - | Orange County SC | 1:3 | ||||
| 5. Round | 30/07/2023 | Loudoun United | - | Miami FC | 1:2 | ||||
| 6. Round | 13/08/2023 | Las Vegas Lights FC | - | Loudoun United | 0:3 | ||||
| 6. Round | 27/08/2023 | Indy Eleven | - | Loudoun United | 2:1 | ||||
| 7. Round | 10/09/2023 | Pittsburgh Riverhounds | - | Loudoun United | 3:1 |
Colombia
USA