1. Round | 10/03/2019 | Memphis 901 | - | Tampa Bay Rowdies | 0:1 | ||||
1. Round | 16/03/2019 | Tampa Bay Rowdies | - | Pittsburgh Riverhounds | 2:0 | ||||
1. Round | 30/03/2019 | Tampa Bay Rowdies | - | Loudoun United | 0:0 | ||||
2. Round | 07/04/2019 | Tampa Bay Rowdies | - | Hartford Athletic | 4:0 | ||||
2. Round | 14/04/2019 | Tampa Bay Rowdies | - | Louisville City FC | 1:1 | ||||
3. Round | 09/05/2019 | Nashville SC | - | Tampa Bay Rowdies | 0:1 | ||||
4. Round | 22/06/2019 | Bethlehem Steel FC | - | Tampa Bay Rowdies | 1:2 | ||||
5. Round | 07/07/2019 | Swope Park Rangers | - | Tampa Bay Rowdies | 1:3 | ||||
5. Round | 21/07/2019 | Tampa Bay Rowdies | - | Saint Louis FC | 4:1 | ||||
7. Round | 01/09/2019 | Tampa Bay Rowdies | - | Nashville SC | 1:2 | ||||
7. Round | 08/09/2019 | Charlotte Independence | - | Tampa Bay Rowdies | 1:3 | ||||
7. Round | 22/09/2019 | Tampa Bay Rowdies | - | Bethlehem Steel FC | 6:1 | ||||
7. Round | 29/09/2019 | Louisville City FC | - | Tampa Bay Rowdies | 2:2 | ||||
8. Round | 05/10/2019 | Loudoun United | - | Tampa Bay Rowdies | 2:0 | ||||
8. Round | 20/10/2019 | Hartford Athletic | - | Tampa Bay Rowdies | 2:1 |