| 1. Round | 08/03/2020 | Atlanta United II | - | Charleston Battery | 0:1 | ||||
| 2. Round | 20/07/2020 | Charleston Battery | - | Birmingham Legion | 1:2 |  |
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| 2. Round | 25/07/2020 | Charleston Battery | - | Atlanta United II | 3:0 |  |
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| 3. Round | 01/08/2020 | Tampa Bay Rowdies | - | Charleston Battery | 2:0 | ||||
| 3. Round | 06/08/2020 | Atlanta United II | - | Charleston Battery | 1:1 | ||||
| 3. Round | 09/08/2020 | Charlotte Independence | - | Charleston Battery | 1:1 | ||||
| 3. Round | 16/08/2020 | Charleston Battery | - | Atlanta United II | 3:2 | ||||
| 3. Round | 20/08/2020 | North Carolina FC | - | Charleston Battery | 0:3 | |
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| 3. Round | 27/08/2020 | Charleston Battery | - | Miami FC | 3:1 | ||||
| 3. Round | 30/08/2020 | Charleston Battery | - | Tampa Bay Rowdies | 1:0 | ||||
| 4. Round | 06/09/2020 | Miami FC | - | Charleston Battery | 1:1 | ||||
| 4. Round | 20/09/2020 | Charleston Battery | - | Miami FC | 2:0 | |
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| 5. Round | 01/10/2020 | Miami FC | - | Charleston Battery | 4:3 | |
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| 5. Round | 04/10/2020 | Tampa Bay Rowdies | - | Charleston Battery | 1:2 |
Jamaica