| 3. Round | 19/05/2019 | San Antonio FC | - | Tulsa Roughnecks | 1:1 | ||||
| 4. Round | 08/06/2019 | Phoenix Rising | - | Tulsa Roughnecks | 5:0 | ||||
| 4. Round | 16/06/2019 | Tulsa Roughnecks | - | El Paso Locomotive | 0:2 |  |
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| 4. Round | 30/06/2019 | Tulsa Roughnecks | - | Real Monarchs SLC | 1:3 | ||||
| 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 |  |
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| 6. Round | 04/08/2019 | OKC Energy FC | - | Tulsa Roughnecks | 1:1 | ||||
| 6. Round | 11/08/2019 | Real Monarchs SLC | - | Tulsa Roughnecks | 4:1 | ||||
| 7. Round | 01/09/2019 | Tulsa Roughnecks | - | Fresno FC | 2:1 | ||||
| 8. Round | 06/10/2019 | Tulsa Roughnecks | - | Sacramento Republic | 2:3 |
USA