| 1. Round | 07/03/2020 | New York RB II | - | Tampa Bay Rowdies | 0:1 | ||||
| 2. Round | 18/07/2020 | New York RB II | - | Hartford Athletic | 0:1 | ||||
| 2. Round | 23/07/2020 | Philadelphia Union 2 | - | New York RB II | 1:5 |  |
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| 2. Round | 26/07/2020 | New York RB II | - | Pittsburgh Riverhounds | 2:1 | |
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| 3. Round | 05/08/2020 | Philadelphia Union 2 | - | New York RB II | 3:2 | ||||
| 3. Round | 16/08/2020 | Hartford Athletic | - | New York RB II | 2:1 | ||||
| 3. Round | 29/08/2020 | Loudoun United | - | New York RB II | 2:3 | ||||
| 4. Round | 05/09/2020 | New York RB II | - | Pittsburgh Riverhounds | 0:3 | ||||
| 4. Round | 09/09/2020 | New York RB II | - | Philadelphia Union 2 | 6:0 | |
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| 4. Round | 17/09/2020 | Hartford Athletic | - | New York RB II | 3:1 | ||||
| 4. Round | 24/09/2020 | Atlanta United II | - | New York RB II | 5:3 | ||||
| 4. Round | 26/09/2020 | New York RB II | - | Philadelphia Union 2 | 5:4 | |
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| 4. Round | 30/09/2020 | New York RB II | - | North Carolina FC | 0:3 | ||||
| 5. Round | 05/10/2020 | New York RB II | - | Hartford Athletic | 0:2 | |
Gambia
USA