| 1. Round | 23/03/2019 | Charlotte Independence | - | Atlanta United II | 3:3 | ||||
| 1. Round | 30/03/2019 | Saint Louis FC | - | Charlotte Independence | 1:0 | ||||
| 2. Round | 07/04/2019 | Charleston Battery | - | Charlotte Independence | 2:0 |  |
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| 2. Round | 14/04/2019 | Charlotte Independence | - | New York RB II | 1:2 | |
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| 2. Round | 17/04/2019 | Charlotte Independence | - | Bethlehem Steel FC | 2:1 | ||||
| 2. Round | 21/04/2019 | Charlotte Independence | - | North Carolina FC | 0:3 | ||||
| 4. Round | 08/06/2019 | Swope Park Rangers | - | Charlotte Independence | 0:0 | ||||
| 4. Round | 23/06/2019 | Louisville City FC | - | Charlotte Independence | 1:1 | ||||
| 4. Round | 30/06/2019 | Charlotte Independence | - | Memphis 901 | 1:0 |
Scotland