| 1. Round | 10/03/2019 | Charleston Battery | - | Ottawa Fury | 1:1 | ||||
| 1. Round | 16/03/2019 | Charleston Battery | - | Hartford Athletic | 2:1 | ||||
| 1. Round | 30/03/2019 | North Carolina FC | - | Charleston Battery | 1:1 |  |
|||
| 2. Round | 07/04/2019 | Charleston Battery | - | Charlotte Independence | 2:0 | ||||
| 2. Round | 21/04/2019 | Charleston Battery | - | Nashville SC | 3:1 | ||||
| 2. Round | 28/04/2019 | Memphis 901 | - | Charleston Battery | 0:1 | ||||
| 6. Round | 04/08/2019 | Charleston Battery | - | Tampa Bay Rowdies | 0:5 | ||||
| 6. Round | 11/08/2019 | Saint Louis FC | - | Charleston Battery | 1:1 | ||||
| 6. Round | 18/08/2019 | Charleston Battery | - | Louisville City FC | 1:2 | ||||
| 6. Round | 31/08/2019 | Charlotte Independence | - | Charleston Battery | 0:0 | |
USA