1. Round | 11/03/2023 | Memphis 901 | - | Loudoun United | 1:3 | ||||
1. Round | 19/03/2023 | Loudoun United | - | San Antonio FC | 1:1 | ||||
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 | 07/05/2023 | Loudoun United | - | Indy Eleven | 1:2 | ||||
3. Round | 14/05/2023 | El Paso Locomotive | - | Loudoun United | 1:0 | ||||
3. Round | 18/05/2023 | Loudoun United | - | New Mexico United | 1:3 | ||||
3. Round | 21/05/2023 | Hartford Athletic | - | Loudoun United | 2:0 | ||||
3. Round | 28/05/2023 | Loudoun United | - | Pittsburgh Riverhounds | 0:1 |