4. Round | 29/06/2019 | Loudoun United | - | Atlanta United II | 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 | ||||
6. Round | 29/08/2019 | Loudoun United | - | Birmingham Legion | 1:1 | ||||
7. Round | 19/09/2019 | Bethlehem Steel FC | - | Loudoun United | 5:2 | ||||
7. Round | 26/09/2019 | Loudoun United | - | Swope Park Rangers | 4:1 | ||||
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 | 13/10/2019 | Charleston Battery | - | Loudoun United | 1:2 |