| 1. Round | 15/03/2019 | Charlotte Independence | - | Indy Eleven | 2:3 | ||||
| 1. Round | 23/03/2019 | Charlotte Independence | - | Atlanta United II | 3:3 |  |
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| 2. Round | 07/04/2019 | Charleston Battery | - | Charlotte Independence | 2:0 | ||||
| 2. Round | 14/04/2019 | Charlotte Independence | - | New York RB II | 1:2 |  |
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| 5. Round | 05/07/2019 | North Carolina FC | - | Charlotte Independence | 1:1 | |
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| 5. Round | 08/07/2019 | Charlotte Independence | - | Pittsburgh Riverhounds | 1:0 | ||||
| 5. Round | 14/07/2019 | Charlotte Independence | - | Saint Louis FC | 2:1 | ||||
| 5. Round | 25/07/2019 | Atlanta United II | - | Charlotte Independence | 2:2 | ||||
| 5. Round | 28/07/2019 | Birmingham Legion | - | Charlotte Independence | 1:0 | |
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| 6. Round | 04/08/2019 | Charlotte Independence | - | Louisville City FC | 0:1 | ||||
| 6. Round | 10/08/2019 | Loudoun United | - | Charlotte Independence | 3:3 | ||||
| 6. Round | 31/08/2019 | Charlotte Independence | - | Charleston Battery | 0:0 | |
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| 7. Round | 22/09/2019 | Charlotte Independence | - | Swope Park Rangers | 0:3 | ||||
| 7. Round | 29/09/2019 | Charlotte Independence | - | Hartford Athletic | 4:0 | |
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| 8. Round | 20/10/2019 | Charlotte Independence | - | Ottawa Fury | 3:1 |
Trinidad & Tobago