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 | 15/08/2019 | Loudoun United | - | Charleston Battery | 1:2 | ||||
6. Round | 18/08/2019 | Loudoun United | - | Ottawa Fury | 1:3 | ||||
7. Round | 01/09/2019 | Loudoun United | - | North Carolina FC | 4:0 | ||||
7. Round | 07/09/2019 | Hartford Athletic | - | Loudoun United | 5:1 | ||||
7. Round | 14/09/2019 | Loudoun United | - | Memphis 901 | 1:2 | ||||
7. Round | 19/09/2019 | Bethlehem Steel FC | - | Loudoun United | 5:2 | ||||
7. Round | 26/09/2019 | Loudoun United | - | Swope Park Rangers | 4:1 | ||||
7. Round | 29/09/2019 | Loudoun United | - | Nashville SC | 0:2 | ||||
8. Round | 02/10/2019 | Loudoun United | - | Pittsburgh Riverhounds | 1:2 | ||||
8. Round | 05/10/2019 | Loudoun United | - | Tampa Bay Rowdies | 2:0 | ||||
8. Round | 10/10/2019 | Loudoun United | - | Saint Louis FC | 4:3 | ||||
8. Round | 13/10/2019 | Charleston Battery | - | Loudoun United | 1:2 | ||||
8. Round | 20/10/2019 | Loudoun United | - | New York RB II | 7:3 |