| 2. Round | 21/04/2019 | Charleston Battery | - | Nashville SC | 3:1 | ||||
| 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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| 3. Round | 12/05/2019 | Charleston Battery | - | Saint Louis FC | 0:0 | ||||
| 3. Round | 26/05/2019 | Charleston Battery | - | Atlanta United II | 1:1 | ||||
| 4. Round | 02/06/2019 | Louisville City FC | - | Charleston Battery | 4:1 | ||||
| 4. Round | 09/06/2019 | Charleston Battery | - | Birmingham Legion | 3:1 |  |
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| 4. Round | 15/06/2019 | Tampa Bay Rowdies | - | Charleston Battery | 1:1 | ||||
| 4. Round | 23/06/2019 | Charleston Battery | - | Swope Park Rangers | 1:1 | ||||
| 4. Round | 30/06/2019 | Charleston Battery | - | New York RB II | 1:1 | |
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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 | ||||
| 8. Round | 06/10/2019 | Birmingham Legion | - | Charleston Battery | 0:0 | ||||
| 8. Round | 13/10/2019 | Charleston Battery | - | Loudoun United | 1:2 | ||||
| 8. Round | 17/10/2019 | Charleston Battery | - | Memphis 901 | 2:0 |
Jamaica