| 2. Round | 17/04/2019 | Charlotte Independence | - | Bethlehem Steel FC | 2:1 | ||||
| 2. Round | 21/04/2019 | Charlotte Independence | - | North Carolina FC | 0:3 | ||||
| 2. Round | 28/04/2019 | Tampa Bay Rowdies | - | Charlotte Independence | 1:1 | ||||
| 3. Round | 05/05/2019 | Hartford Athletic | - | Charlotte Independence | 1:1 | ||||
| 3. Round | 12/05/2019 | Charlotte Independence | - | Loudoun United | 1:3 | ||||
| 3. Round | 19/05/2019 | Nashville SC | - | Charlotte Independence | 1:1 | ||||
| 3. Round | 26/05/2019 | Pittsburgh Riverhounds | - | Charlotte Independence | 0:0 | ||||
| 4. Round | 02/06/2019 | Ottawa Fury | - | Charlotte Independence | 4:1 | ||||
| 4. Round | 16/06/2019 | Charlotte Independence | - | Birmingham Legion | 4:1 | ||||
| 6. Round | 04/08/2019 | Charlotte Independence | - | Louisville City FC | 0:1 |
England