| 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 |  |
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| 1. Round | 30/03/2019 | Indy Eleven | - | Hartford Athletic | 1:0 | ||||
| 2. Round | 14/04/2019 | Pittsburgh Riverhounds | - | Hartford Athletic | 3:1 | |
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| 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 | 11/05/2019 | Hartford Athletic | - | Memphis 901 | 1:2 | ||||
| 3. Round | 19/05/2019 | Loudoun United | - | Hartford Athletic | 1:2 | ||||
| 4. Round | 29/06/2019 | Hartford Athletic | - | Bethlehem Steel FC | 0:3 | |
Denmark