| 1. Round | 10/03/2019 | Atlanta United II | - | Hartford Athletic | 2:0 | ||||
| 1. Round | 16/03/2019 | Charleston Battery | - | Hartford Athletic | 2:1 | ||||
| 1. Round | 23/03/2019 | Louisville City FC | - | Hartford Athletic | 2:1 | ||||
| 1. Round | 30/03/2019 | Indy Eleven | - | Hartford Athletic | 1:0 | ||||
| 2. Round | 07/04/2019 | Tampa Bay Rowdies | - | Hartford Athletic | 4:0 | ||||
| 2. Round | 18/04/2019 | New York RB II | - | Hartford Athletic | 4:0 | ||||
| 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 | ||||
| 4. Round | 09/06/2019 | Hartford Athletic | - | Saint Louis FC | 2:1 | ||||
| 4. Round | 16/06/2019 | Hartford Athletic | - | Nashville SC | 2:3 | ||||
| 5. Round | 07/07/2019 | Memphis 901 | - | Hartford Athletic | 4:1 | ||||
| 5. Round | 13/07/2019 | Hartford Athletic | - | Indy Eleven | 2:1 | ||||
| 5. Round | 18/07/2019 | Swope Park Rangers | - | Hartford Athletic | 4:3 | |
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| 5. Round | 20/07/2019 | Hartford Athletic | - | Charleston Battery | 2:3 |
USA