| 1. Round | 21/03/2019 | New Mexico United | - | Tulsa Roughnecks | 2:1 | ||||
| 1. Round | 23/03/2019 | Tulsa Roughnecks | - | Tacoma Defiance | 4:0 | ||||
| 1. Round | 30/03/2019 | Tulsa Roughnecks | - | Rio Grande Valley FC | 2:1 | ||||
| 2. Round | 07/04/2019 | Los Angeles Galaxy II | - | Tulsa Roughnecks | 4:2 | ||||
| 2. Round | 25/04/2019 | Tulsa Roughnecks | - | Colorado Springs Switchbacks | 2:0 | ||||
| 2. Round | 28/04/2019 | Tulsa Roughnecks | - | OKC Energy FC | 1:1 | ||||
| 3. Round | 05/05/2019 | Reno 1868 FC | - | Tulsa Roughnecks | 2:2 | ||||
| 3. Round | 19/05/2019 | San Antonio FC | - | Tulsa Roughnecks | 1:1 |
Jamaica