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 | ||||
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 | 15/06/2019 | Tampa Bay Rowdies | - | Charleston Battery | 1:1 | ||||
4. Round | 22/06/2019 | Bethlehem Steel FC | - | Tampa Bay Rowdies | 1:2 | ||||
4. Round | 30/06/2019 | Tampa Bay Rowdies | - | Ottawa Fury | 2:1 | ||||
5. Round | 07/07/2019 | Swope Park Rangers | - | Tampa Bay Rowdies | 1:3 |