| 5. Round | 07/07/2019 | Portland Timbers 2 | - | Tulsa Roughnecks | 1:1 |  |
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| 5. Round | 14/07/2019 | Colorado Springs Switchbacks | - | Tulsa Roughnecks | 1:0 | ||||
| 5. Round | 25/07/2019 | Tulsa Roughnecks | - | Los Angeles Galaxy II | 1:3 | ||||
| 5. Round | 28/07/2019 | Tulsa Roughnecks | - | Phoenix Rising | 0:1 | ||||
| 6. Round | 04/08/2019 | OKC Energy FC | - | Tulsa Roughnecks | 1:1 | |
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| 6. Round | 18/08/2019 | Austin Bold | - | Tulsa Roughnecks | 5:1 | ||||
| 7. Round | 01/09/2019 | Tulsa Roughnecks | - | Fresno FC | 2:1 | ||||
| 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 | ||||
| 7. Round | 26/09/2019 | Tulsa Roughnecks | - | San Antonio FC | 4:3 |
USA