| 2. Round | 03/05/2021 | Miami FC | - | Loudoun United | 2:1 | ||||
| 2. Round | 23/05/2021 | Tampa Bay Rowdies | - | Miami FC | 2:1 | ||||
| 3. Round | 06/06/2021 | Miami FC | - | Rio Grande Valley FC | 2:4 | ||||
| 3. Round | 13/06/2021 | Pittsburgh Riverhounds | - | Miami FC | 1:1 | ||||
| 4. Round | 08/07/2021 | Miami FC | - | Tampa Bay Rowdies | 2:1 | ||||
| 4. Round | 11/07/2021 | Loudoun United | - | Miami FC | 1:4 |  |
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| 4. Round | 18/07/2021 | Miami FC | - | Tampa Bay Rowdies | 2:1 | ||||
| 4. Round | 25/07/2021 | Hartford Athletic | - | Miami FC | 2:0 | ||||
| 5. Round | 02/08/2021 | Miami FC | - | Charleston Battery | 3:2 | ||||
| 5. Round | 05/08/2021 | Hartford Athletic | - | Miami FC | 1:1 | ||||
| 5. Round | 11/08/2021 | Pittsburgh Riverhounds | - | Miami FC | 2:3 | ||||
| 5. Round | 15/08/2021 | Austin Bold | - | Miami FC | 0:0 | ||||
| 5. Round | 29/08/2021 | Miami FC | - | New York RB II | 3:0 | ||||
| 6. Round | 05/09/2021 | Charlotte Independence | - | Miami FC | 2:2 | ||||
| 6. Round | 12/09/2021 | Memphis 901 | - | Miami FC | 0:2 |
Jamaica