| 2. Round | 06/04/2019 | Swope Park Rangers | - | Bethlehem Steel FC | 3:4 | ||||
| 2. Round | 16/04/2019 | Swope Park Rangers | - | Indy Eleven | 1:3 | ||||
| 2. Round | 20/04/2019 | Birmingham Legion | - | Swope Park Rangers | 0:0 | ||||
| 2. Round | 28/04/2019 | Saint Louis FC | - | Swope Park Rangers | 3:1 | ||||
| 3. Round | 07/05/2019 | Swope Park Rangers | - | Louisville City FC | 3:2 | ||||
| 3. Round | 12/05/2019 | Nashville SC | - | Swope Park Rangers | 5:1 | ||||
| 3. Round | 19/05/2019 | Swope Park Rangers | - | Atlanta United II | 1:1 | ||||
| 3. Round | 26/05/2019 | Tampa Bay Rowdies | - | Swope Park Rangers | 1:0 | ||||
| 4. Round | 06/06/2019 | Swope Park Rangers | - | Loudoun United | 2:3 | ||||
| 4. Round | 23/06/2019 | Charleston Battery | - | Swope Park Rangers | 1:1 | ||||
| 4. Round | 30/06/2019 | Swope Park Rangers | - | Saint Louis FC | 2:1 | ||||
| 5. Round | 07/07/2019 | Swope Park Rangers | - | Tampa Bay Rowdies | 1:3 | ||||
| 6. Round | 04/08/2019 | Swope Park Rangers | - | Nashville SC | 0:2 |
USA