| 1. Round | 08/03/2020 | Atlanta United II | - | Charleston Battery | 0:1 | ||||
| 3. Round | 06/08/2020 | Atlanta United II | - | Charleston Battery | 1:1 | ||||
| 3. Round | 09/08/2020 | Charlotte Independence | - | Charleston Battery | 1:1 |  |
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| 5. Round | 04/10/2020 | Tampa Bay Rowdies | - | Charleston Battery | 1:2 |
Jamaica