| 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 | 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 |  |
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| 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 | ||||
| 5. Round | 21/07/2019 | Tampa Bay Rowdies | - | Saint Louis FC | 4:1 | ||||
| 5. Round | 27/07/2019 | New York RB II | - | Tampa Bay Rowdies | 2:0 | ||||
| 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 | 13/10/2019 | Tampa Bay Rowdies | - | Indy Eleven | 1:1 | ||||
| 8. Round | 20/10/2019 | Hartford Athletic | - | Tampa Bay Rowdies | 2:1 |
Ivory Coast