| 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 | ||||
| 1. Round | 30/03/2019 | Tampa Bay Rowdies | - | Loudoun United | 0:0 | ||||
| 2. Round | 14/04/2019 | Tampa Bay Rowdies | - | Louisville City FC | 1:1 | ||||
| 2. Round | 28/04/2019 | Tampa Bay Rowdies | - | Charlotte Independence | 1:1 | ||||
| 3. Round | 02/05/2019 | Indy Eleven | - | Tampa Bay Rowdies | 0:0 |  |
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| 4. Round | 22/06/2019 | Bethlehem Steel FC | - | Tampa Bay Rowdies | 1:2 | ||||
| 5. Round | 14/07/2019 | Pittsburgh Riverhounds | - | Tampa Bay Rowdies | 1:1 |
USA