| 1. Round | 10/03/2019 | Birmingham Legion | - | Bethlehem Steel FC | 0:2 | ||||
| 3. Round | 02/05/2019 | New York RB II | - | Birmingham Legion | 5:0 | ||||
| 6. Round | 29/08/2019 | Loudoun United | - | Birmingham Legion | 1:1 | ||||
| 7. Round | 05/09/2019 | Atlanta United II | - | Birmingham Legion | 0:5 | ||||
| 8. Round | 01/10/2019 | Swope Park Rangers | - | Birmingham Legion | 3:1 | ||||
| 8. Round | 06/10/2019 | Birmingham Legion | - | Charleston Battery | 0:0 |  |
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| 8. Round | 20/10/2019 | Birmingham Legion | - | Pittsburgh Riverhounds | 0:1 | |
USA