| 4. Round | 25/07/2021 | Tampa Bay Rowdies | - | Loudoun United | 3:1 | ||||
| 4. Round | 01/08/2021 | Charlotte Independence | - | Tampa Bay Rowdies | 2:0 | ||||
| 5. Round | 07/08/2021 | New York RB II | - | Tampa Bay Rowdies | 1:2 | ||||
| 5. Round | 14/08/2021 | Tampa Bay Rowdies | - | Hartford Athletic | 1:0 | ||||
| 5. Round | 18/08/2021 | Pittsburgh Riverhounds | - | Tampa Bay Rowdies | 0:0 |  |
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| 5. Round | 24/08/2021 | Loudoun United | - | Tampa Bay Rowdies | 0:2 | |
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| 5. Round | 29/08/2021 | Tampa Bay Rowdies | - | Charlotte Independence | 2:0 | ||||
| 6. Round | 04/09/2021 | Tampa Bay Rowdies | - | Oakland Roots | 3:0 |  |
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| 6. Round | 08/09/2021 | Charleston Battery | - | Tampa Bay Rowdies | 0:1 | ||||
| 6. Round | 12/09/2021 | Tampa Bay Rowdies | - | New York RB II | 6:0 | ||||
| 6. Round | 19/09/2021 | Atlanta United II | - | Tampa Bay Rowdies | 0:2 | ||||
| 7. Round | 31/10/2021 | Las Vegas Lights FC | - | Tampa Bay Rowdies | 1:2 |
Zimbabwe