| 1. Round | 10/03/2019 | Charleston Battery | - | Ottawa Fury | 1:1 | ||||
| 1. Round | 16/03/2019 | Charleston Battery | - | Hartford Athletic | 2:1 |  |
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| 1. Round | 30/03/2019 | North Carolina FC | - | Charleston Battery | 1:1 | ||||
| 2. Round | 07/04/2019 | Charleston Battery | - | Charlotte Independence | 2:0 | ||||
| 2. Round | 14/04/2019 | Bethlehem Steel FC | - | Charleston Battery | 3:1 | ||||
| 2. Round | 21/04/2019 | Charleston Battery | - | Nashville SC | 3:1 | |
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| 2. Round | 28/04/2019 | Memphis 901 | - | Charleston Battery | 0:1 | ||||
| 3. Round | 05/05/2019 | Charleston Battery | - | Pittsburgh Riverhounds | 2:2 | |
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| 5. Round | 20/07/2019 | Hartford Athletic | - | Charleston Battery | 2:3 | ||||
| 6. Round | 11/08/2019 | Saint Louis FC | - | Charleston Battery | 1:1 | |
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| 6. Round | 15/08/2019 | Loudoun United | - | Charleston Battery | 1:2 | |
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| 7. Round | 08/09/2019 | Charleston Battery | - | Indy Eleven | 1:0 | |
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| 7. Round | 19/09/2019 | Atlanta United II | - | Charleston Battery | 3:1 | ||||
| 7. Round | 28/09/2019 | New York RB II | - | Charleston Battery | 1:1 | |
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| 8. Round | 13/10/2019 | Charleston Battery | - | Loudoun United | 1:2 | |
Jamaica