| 4. Round | 10/06/2018 | Richmond Kickers | - | Charleston Battery | 2:0 | ||||
| 4. Round | 24/06/2018 | Charleston Battery | - | Pittsburgh Riverhounds | 0:0 | ||||
| 5. Round | 08/07/2018 | North Carolina FC | - | Charleston Battery | 1:1 | ||||
| 5. Round | 12/07/2018 | Charleston Battery | - | Indy Eleven | 2:1 | ||||
| 5. Round | 15/07/2018 | Charleston Battery | - | Louisville City FC | 2:1 | ||||
| 5. Round | 22/07/2018 | Pittsburgh Riverhounds | - | Charleston Battery | 0:1 | ||||
| 5. Round | 29/07/2018 | Charleston Battery | - | Richmond Kickers | 3:0 | ||||
| 6. Round | 12/08/2018 | Charleston Battery | - | Atlanta United II | 1:0 | ||||
| 6. Round | 26/08/2018 | Charleston Battery | - | New York RB II | 4:4 | ||||
| 7. Round | 09/09/2018 | Charleston Battery | - | Tampa Bay Rowdies | 1:0 |  |
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| 7. Round | 20/09/2018 | Charleston Battery | - | Charlotte Independence | 1:1 | ||||
| 7. Round | 27/09/2018 | Charleston Battery | - | North Carolina FC | 2:0 | ||||
| 7. Round | 30/09/2018 | Charleston Battery | - | Toronto FC 2 | 1:2 |
Trinidad & Tobago