| 6. Round | 24/08/2019 | Hartford Athletic | - | Atlanta United II | 3:2 | ||||
| 7. Round | 02/09/2019 | Saint Louis FC | - | Hartford Athletic | 3:2 | ||||
| 7. Round | 07/09/2019 | Hartford Athletic | - | Loudoun United | 5:1 | ||||
| 7. Round | 15/09/2019 | Hartford Athletic | - | Louisville City FC | 0:1 | ||||
| 7. Round | 22/09/2019 | Ottawa Fury | - | Hartford Athletic | 4:1 | ||||
| 7. Round | 29/09/2019 | Charlotte Independence | - | Hartford Athletic | 4:0 | ||||
| 8. Round | 06/10/2019 | Hartford Athletic | - | Swope Park Rangers | 2:2 | ||||
| 8. Round | 10/10/2019 | Hartford Athletic | - | Birmingham Legion | 4:0 | ||||
| 8. Round | 20/10/2019 | Hartford Athletic | - | Tampa Bay Rowdies | 2:1 |
USA
England