5. Round | 29/07/2019 | Loudoun United | - | Louisville City FC | 3:0 | ||||
6. Round | 03/08/2019 | Atlanta United II | - | Loudoun United | 4:2 | ||||
6. Round | 10/08/2019 | Loudoun United | - | Charlotte Independence | 3:3 | ||||
6. Round | 18/08/2019 | Loudoun United | - | Ottawa Fury | 1:3 | ||||
6. Round | 29/08/2019 | Loudoun United | - | Birmingham Legion | 1:1 | ||||
7. Round | 14/09/2019 | Loudoun United | - | Memphis 901 | 1:2 | ||||
7. Round | 19/09/2019 | Bethlehem Steel FC | - | Loudoun United | 5:2 |