| 2. Round | 28/04/2019 | North Carolina FC | - | Hartford Athletic | 4:1 | ||||
| 3. Round | 05/05/2019 | Hartford Athletic | - | Charlotte Independence | 1:1 |  |
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| 3. Round | 11/05/2019 | Hartford Athletic | - | Memphis 901 | 1:2 | ||||
| 3. Round | 19/05/2019 | Loudoun United | - | Hartford Athletic | 1:2 | ||||
| 3. Round | 26/05/2019 | Hartford Athletic | - | Ottawa Fury | 1:1 | |
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| 4. Round | 02/06/2019 | Hartford Athletic | - | North Carolina FC | 1:1 | ||||
| 6. Round | 08/08/2019 | Nashville SC | - | Hartford Athletic | 4:0 |
USA