| 1. Round | 16/03/2019 | Tampa Bay Rowdies | - | Pittsburgh Riverhounds | 2:0 | ||||
| 1. Round | 23/03/2019 | Saint Louis FC | - | Tampa Bay Rowdies | 1:1 | ||||
| 2. Round | 07/04/2019 | Tampa Bay Rowdies | - | Hartford Athletic | 4:0 | ||||
| 2. Round | 25/04/2019 | Atlanta United II | - | Tampa Bay Rowdies | 1:4 |  |
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| 2. Round | 28/04/2019 | Tampa Bay Rowdies | - | Charlotte Independence | 1:1 | ||||
| 3. Round | 02/05/2019 | Indy Eleven | - | Tampa Bay Rowdies | 0:0 | ||||
| 4. Round | 09/06/2019 | Tampa Bay Rowdies | - | North Carolina FC | 1:3 | ||||
| 4. Round | 15/06/2019 | Tampa Bay Rowdies | - | Charleston Battery | 1:1 |
USA