| 1. Round | 09/03/2019 | New York RB II | - | Swope Park Rangers | 3:1 | ||||
| 2. Round | 28/04/2019 | New York RB II | - | Indy Eleven | 2:1 | ||||
| 4. Round | 16/06/2019 | New York RB II | - | Louisville City FC | 1:0 | ||||
| 4. Round | 30/06/2019 | Charleston Battery | - | New York RB II | 1:1 | ||||
| 5. Round | 06/07/2019 | New York RB II | - | Ottawa Fury | 1:1 | ||||
| 5. Round | 21/07/2019 | Memphis 901 | - | New York RB II | 2:2 |  |
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| 6. Round | 03/08/2019 | New York RB II | - | Saint Louis FC | 2:0 | ||||
| 6. Round | 10/08/2019 | Hartford Athletic | - | New York RB II | 1:5 | |
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| 6. Round | 15/08/2019 | New York RB II | - | Pittsburgh Riverhounds | 1:2 | ||||
| 6. Round | 22/08/2019 | Nashville SC | - | New York RB II | 1:2 | ||||
| 7. Round | 05/09/2019 | Indy Eleven | - | New York RB II | 1:0 | ||||
| 7. Round | 14/09/2019 | New York RB II | - | Charlotte Independence | 2:0 | ||||
| 7. Round | 22/09/2019 | Louisville City FC | - | New York RB II | 5:3 | |
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| 8. Round | 06/10/2019 | North Carolina FC | - | New York RB II | 2:0 | ||||
| 8. Round | 17/10/2019 | Birmingham Legion | - | New York RB II | 2:1 | ||||
| 8. Round | 20/10/2019 | Loudoun United | - | New York RB II | 7:3 |
France