1. Round | 23/03/2019 | Saint Louis FC | - | Tampa Bay Rowdies | 1:1 | ||||
2. Round | 25/04/2019 | Atlanta United II | - | Tampa Bay Rowdies | 1:4 | ||||
3. Round | 02/05/2019 | Indy Eleven | - | Tampa Bay Rowdies | 0:0 | ||||
3. Round | 09/05/2019 | Nashville SC | - | Tampa Bay Rowdies | 0:1 | ||||
3. Round | 19/05/2019 | Tampa Bay Rowdies | - | New York RB II | 2:0 | ||||
3. Round | 26/05/2019 | Tampa Bay Rowdies | - | Swope Park Rangers | 1:0 | ||||
4. Round | 02/06/2019 | Birmingham Legion | - | Tampa Bay Rowdies | 0:2 | ||||
4. Round | 09/06/2019 | Tampa Bay Rowdies | - | North Carolina FC | 1:3 | ||||
5. Round | 21/07/2019 | Tampa Bay Rowdies | - | Saint Louis FC | 4:1 | ||||
6. Round | 04/08/2019 | Charleston Battery | - | Tampa Bay Rowdies | 0:5 | ||||
6. Round | 22/08/2019 | North Carolina FC | - | Tampa Bay Rowdies | 4:2 | ||||
6. Round | 25/08/2019 | Tampa Bay Rowdies | - | Memphis 901 | 5:0 | ||||
7. Round | 19/09/2019 | Ottawa Fury | - | Tampa Bay Rowdies | 1:0 |