| 1. Round | 07/03/2020 | New York RB II | - | Tampa Bay Rowdies | 0:1 | ||||
| 2. Round | 12/07/2020 | Tampa Bay Rowdies | - | Atlanta United II | 2:1 | ||||
| 2. Round | 26/07/2020 | Birmingham Legion | - | Tampa Bay Rowdies | 1:1 | ||||
| 3. Round | 01/08/2020 | Tampa Bay Rowdies | - | Charleston Battery | 2:0 | ||||
| 3. Round | 08/08/2020 | Miami FC | - | Tampa Bay Rowdies | 0:3 | ||||
| 3. Round | 13/08/2020 | Atlanta United II | - | Tampa Bay Rowdies | 0:2 | ||||
| 3. Round | 17/08/2020 | Tampa Bay Rowdies | - | Miami FC | 1:1 | ||||
| 3. Round | 30/08/2020 | Charleston Battery | - | Tampa Bay Rowdies | 1:0 | ||||
| 4. Round | 03/09/2020 | Tampa Bay Rowdies | - | Miami FC | 3:0 | ||||
| 4. Round | 07/09/2020 | Tampa Bay Rowdies | - | Philadelphia Union 2 | 2:0 | ||||
| 4. Round | 12/09/2020 | Charleston Battery | - | Tampa Bay Rowdies | 1:0 |  |
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| 5. Round | 04/10/2020 | Tampa Bay Rowdies | - | Charleston Battery | 1:2 | |
Ghana