| 3. Round | 26/05/2019 | Hartford Athletic | - | Ottawa Fury | 1:1 | ||||
| 4. Round | 02/06/2019 | Hartford Athletic | - | North Carolina FC | 1:1 | ||||
| 4. Round | 09/06/2019 | Hartford Athletic | - | Saint Louis FC | 2:1 | ||||
| 4. Round | 16/06/2019 | Hartford Athletic | - | Nashville SC | 2:3 |  |
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| 4. Round | 23/06/2019 | Birmingham Legion | - | Hartford Athletic | 2:2 |  |
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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 | |
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| 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 | ||||
| 8. Round | 06/10/2019 | Hartford Athletic | - | Swope Park Rangers | 2:2 | |
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| 8. Round | 10/10/2019 | Hartford Athletic | - | Birmingham Legion | 4:0 | ||||
| 8. Round | 20/10/2019 | Hartford Athletic | - | Tampa Bay Rowdies | 2:1 | |
USA