1. Round | 10/03/2019 | Memphis 901 | - | Tampa Bay Rowdies | 0:1 | ||||
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 | 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 | 28/04/2019 | Tampa Bay Rowdies | - | Charlotte Independence | 1:1 | ||||
3. Round | 02/05/2019 | Indy Eleven | - | Tampa Bay Rowdies | 0:0 | ||||
3. Round | 26/05/2019 | Tampa Bay Rowdies | - | Swope Park Rangers | 1:0 | ||||
4. Round | 09/06/2019 | Tampa Bay Rowdies | - | North Carolina FC | 1:3 |