| 1. Round | 19/03/2023 | Orange County SC | - | Tampa Bay Rowdies | 1:1 | ||||
| 1. Round | 25/03/2023 | Charleston Battery | - | Tampa Bay Rowdies | 3:0 | ||||
| 2. Round | 02/04/2023 | Tampa Bay Rowdies | - | Birmingham Legion | 0:2 | ||||
| 2. Round | 09/04/2023 | Tampa Bay Rowdies | - | Miami FC | 2:0 |  |
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| 2. Round | 13/04/2023 | Tampa Bay Rowdies | - | Charleston Battery | 1:2 | ||||
| 2. Round | 23/04/2023 | San Diego Loyal | - | Tampa Bay Rowdies | 1:0 | ||||
| 3. Round | 07/05/2023 | Tampa Bay Rowdies | - | Phoenix Rising | 2:0 | ||||
| 3. Round | 14/05/2023 | Tampa Bay Rowdies | - | Detroit City FC | 5:1 | ||||
| 3. Round | 21/05/2023 | Rio Grande Valley FC | - | Tampa Bay Rowdies | 0:3 | ||||
| 4. Round | 11/06/2023 | Tampa Bay Rowdies | - | New Mexico United | 3:2 | ||||
| 5. Round | 30/07/2023 | Tampa Bay Rowdies | - | FC Tulsa | 3:0 | ||||
| 6. Round | 13/08/2023 | Tampa Bay Rowdies | - | Monterey Bay FC | 4:1 |
Germany