2. Round | 02/05/2021 | Tampa Bay Rowdies | - | Charlotte Independence | 3:0 | ||||
2. Round | 23/05/2021 | Tampa Bay Rowdies | - | Miami FC | 2:1 | ||||
3. Round | 06/06/2021 | Charlotte Independence | - | Tampa Bay Rowdies | 1:0 | ||||
3. Round | 12/06/2021 | Tampa Bay Rowdies | - | Loudoun United | 2:1 | ||||
3. Round | 20/06/2021 | Tampa Bay Rowdies | - | Pittsburgh Riverhounds | 1:2 | ||||
4. Round | 03/07/2021 | Tampa Bay Rowdies | - | Charleston Battery | 1:0 | ||||
4. Round | 08/07/2021 | Miami FC | - | Tampa Bay Rowdies | 2:1 | ||||
4. Round | 14/07/2021 | Tampa Bay Rowdies | - | Hartford Athletic | 0:1 | ||||
4. Round | 18/07/2021 | Miami FC | - | Tampa Bay Rowdies | 2:1 | ||||
5. Round | 14/08/2021 | Tampa Bay Rowdies | - | Hartford Athletic | 1:0 | ||||
5. Round | 24/08/2021 | Loudoun United | - | Tampa Bay Rowdies | 0:2 | ||||
7. Round | 21/10/2021 | Tampa Bay Rowdies | - | Miami FC | 3:0 |