| 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 | 07/04/2019 | Tampa Bay Rowdies | - | Hartford Athletic | 4:0 | ||||
| 2. Round | 14/04/2019 | Pittsburgh Riverhounds | - | Hartford Athletic | 3:1 | ||||
| 2. Round | 28/04/2019 | North Carolina FC | - | Hartford Athletic | 4:1 | ||||
| 3. Round | 05/05/2019 | Hartford Athletic | - | Charlotte Independence | 1:1 | ||||
| 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 | ||||
| 4. Round | 02/06/2019 | Hartford Athletic | - | North Carolina FC | 1:1 |
Wales