| 5. Round | 20/07/2019 | Hartford Athletic | - | Charleston Battery | 2:3 |  |
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| 6. Round | 04/08/2019 | Charleston Battery | - | Tampa Bay Rowdies | 0:5 |  |
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| 6. Round | 15/08/2019 | Loudoun United | - | Charleston Battery | 1:2 | ||||
| 6. Round | 18/08/2019 | Charleston Battery | - | Louisville City FC | 1:2 | |
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| 7. Round | 15/09/2019 | Pittsburgh Riverhounds | - | Charleston Battery | 1:0 |  |
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| 7. Round | 19/09/2019 | Atlanta United II | - | Charleston Battery | 3:1 | ||||
| 7. Round | 22/09/2019 | Charleston Battery | - | North Carolina FC | 2:1 | ||||
| 7. Round | 28/09/2019 | New York RB II | - | Charleston Battery | 1:1 | |
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| 8. Round | 06/10/2019 | Birmingham Legion | - | Charleston Battery | 0:0 |  |
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| 8. Round | 19/10/2019 | Charleston Battery | - | Bethlehem Steel FC | 5:1 | |
Trinidad & Tobago