| 5. Round | 21/07/2019 | Birmingham Legion | - | Atlanta United II | 4:0 | ||||
| 5. Round | 28/07/2019 | Birmingham Legion | - | Charlotte Independence | 1:0 |  |
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| 6. Round | 03/08/2019 | Ottawa Fury | - | Birmingham Legion | 0:0 | |
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| 6. Round | 11/08/2019 | Tampa Bay Rowdies | - | Birmingham Legion | 0:1 | ||||
| 6. Round | 18/08/2019 | Birmingham Legion | - | Memphis 901 | 1:0 | ||||
| 6. Round | 25/08/2019 | Bethlehem Steel FC | - | Birmingham Legion | 2:3 | ||||
| 6. Round | 29/08/2019 | Loudoun United | - | Birmingham Legion | 1:1 | ||||
| 7. Round | 05/09/2019 | Atlanta United II | - | Birmingham Legion | 0:5 | |
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| 7. Round | 14/09/2019 | Birmingham Legion | - | Saint Louis FC | 0:2 | |
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| 7. Round | 21/09/2019 | Birmingham Legion | - | Indy Eleven | 1:0 | |
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| 8. Round | 01/10/2019 | Swope Park Rangers | - | Birmingham Legion | 3:1 | |
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| 8. Round | 06/10/2019 | Birmingham Legion | - | Charleston Battery | 0:0 | ||||
| 8. Round | 10/10/2019 | Hartford Athletic | - | Birmingham Legion | 4:0 | ||||
| 8. Round | 17/10/2019 | Birmingham Legion | - | New York RB II | 2:1 |
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