| 2. Round | 23/04/2023 | San Diego Loyal | - | Tampa Bay Rowdies | 1:0 | ||||
| 2. Round | 29/04/2023 | Detroit City FC | - | Tampa Bay Rowdies | 0:1 | ||||
| 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 | ||||
| 3. Round | 28/05/2023 | Tampa Bay Rowdies | - | Colorado Springs Switchbacks | 2:1 | ||||
| 4. Round | 04/06/2023 | Tampa Bay Rowdies | - | Sacramento Republic | 1:1 | ||||
| 4. Round | 11/06/2023 | Tampa Bay Rowdies | - | New Mexico United | 3:2 |  |
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| 4. Round | 18/06/2023 | El Paso Locomotive | - | Tampa Bay Rowdies | 1:1 |
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