| 1. Round | 10/03/2019 | Birmingham Legion | - | Bethlehem Steel FC | 0:2 | ||||
| 2. Round | 28/04/2019 | Birmingham Legion | - | Loudoun United | 1:0 | ||||
| 3. Round | 02/05/2019 | New York RB II | - | Birmingham Legion | 5:0 | ||||
| 3. Round | 04/05/2019 | Memphis 901 | - | Birmingham Legion | 2:2 | ||||
| 3. Round | 12/05/2019 | Birmingham Legion | - | Louisville City FC | 0:3 | ||||
| 4. Round | 23/06/2019 | Birmingham Legion | - | Hartford Athletic | 2:2 | ||||
| 4. Round | 27/06/2019 | Indy Eleven | - | Birmingham Legion | 3:0 |  |
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| 6. Round | 11/08/2019 | Tampa Bay Rowdies | - | Birmingham Legion | 0:1 | ||||
| 7. Round | 18/09/2019 | Nashville SC | - | Birmingham Legion | 1:0 | ||||
| 7. Round | 21/09/2019 | Birmingham Legion | - | Indy Eleven | 1:0 | ||||
| 8. Round | 20/10/2019 | Birmingham Legion | - | Pittsburgh Riverhounds | 0:1 |
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