| 1. Round | 10/03/2019 | Tulsa Roughnecks | - | Portland Timbers 2 | 1:1 | ||||
| 1. Round | 17/03/2019 | Orange County SC | - | Tulsa Roughnecks | 3:5 | ||||
| 1. Round | 21/03/2019 | New Mexico United | - | Tulsa Roughnecks | 2:1 | ||||
| 1. Round | 23/03/2019 | Tulsa Roughnecks | - | Tacoma Defiance | 4:0 | ||||
| 4. Round | 08/06/2019 | Phoenix Rising | - | Tulsa Roughnecks | 5:0 | ||||
| 4. Round | 16/06/2019 | Tulsa Roughnecks | - | El Paso Locomotive | 0:2 | ||||
| 6. Round | 04/08/2019 | OKC Energy FC | - | Tulsa Roughnecks | 1:1 | ||||
| 6. Round | 11/08/2019 | Real Monarchs SLC | - | Tulsa Roughnecks | 4:1 | ||||
| 6. Round | 29/08/2019 | Tulsa Roughnecks | - | Las Vegas Lights FC | 1:1 | ||||
| 7. Round | 01/09/2019 | Tulsa Roughnecks | - | Fresno FC | 2:1 |  |
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| 7. Round | 05/09/2019 | El Paso Locomotive | - | Tulsa Roughnecks | 2:2 | ||||
| 7. Round | 08/09/2019 | Rio Grande Valley FC | - | Tulsa Roughnecks | 0:1 | ||||
| 7. Round | 22/09/2019 | Tulsa Roughnecks | - | Orange County SC | 0:1 | ||||
| 8. Round | 06/10/2019 | Tulsa Roughnecks | - | Sacramento Republic | 2:3 | ||||
| 8. Round | 13/10/2019 | Tulsa Roughnecks | - | New Mexico United | 2:1 | ||||
| 8. Round | 19/10/2019 | Tulsa Roughnecks | - | Reno 1868 FC | 0:3 |
USA