4. Round | 06/06/2019 | Swope Park Rangers | - | Loudoun United | 2:3 | ||||
4. Round | 09/06/2019 | Louisville City FC | - | Loudoun United | 2:1 | ||||
5. Round | 07/07/2019 | Saint Louis FC | - | Loudoun United | 2:2 | ||||
5. Round | 18/07/2019 | North Carolina FC | - | Loudoun United | 3:0 | ||||
5. Round | 21/07/2019 | Indy Eleven | - | Loudoun United | 2:0 | ||||
5. Round | 29/07/2019 | Loudoun United | - | Louisville City FC | 3:0 | ||||
6. Round | 10/08/2019 | Loudoun United | - | Charlotte Independence | 3:3 | ||||
6. Round | 18/08/2019 | Loudoun United | - | Ottawa Fury | 1:3 | ||||
6. Round | 24/08/2019 | Pittsburgh Riverhounds | - | Loudoun United | 1:0 | ||||
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 | 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 | 20/10/2019 | Loudoun United | - | New York RB II | 7:3 |