| 5. Round | 20/07/2019 | Hartford Athletic | - | Charleston Battery | 2:3 | ||||
| 5. Round | 27/07/2019 | Hartford Athletic | - | Pittsburgh Riverhounds | 2:4 | ||||
| 6. Round | 01/08/2019 | Bethlehem Steel FC | - | Hartford Athletic | 0:3 |  |
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| 6. Round | 08/08/2019 | Nashville SC | - | Hartford Athletic | 4:0 | ||||
| 6. Round | 10/08/2019 | Hartford Athletic | - | New York RB II | 1:5 | ||||
| 7. Round | 22/09/2019 | Ottawa Fury | - | Hartford Athletic | 4:1 | ||||
| 7. Round | 29/09/2019 | Charlotte Independence | - | Hartford Athletic | 4:0 | ||||
| 8. Round | 10/10/2019 | Hartford Athletic | - | Birmingham Legion | 4:0 | |
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| 8. Round | 20/10/2019 | Hartford Athletic | - | Tampa Bay Rowdies | 2:1 |
Colombia
USA