1. Round | 10/03/2019 | Nashville SC | - | Loudoun United | 2:0 | ||||
1. Round | 17/03/2019 | Memphis 901 | - | Loudoun United | 1:1 | ||||
1. Round | 30/03/2019 | Tampa Bay Rowdies | - | Loudoun United | 0:0 | ||||
5. Round | 07/07/2019 | Saint Louis FC | - | Loudoun United | 2:2 | ||||
6. Round | 15/08/2019 | Loudoun United | - | Charleston Battery | 1:2 | ||||
6. Round | 29/08/2019 | Loudoun United | - | Birmingham Legion | 1:1 |