| 4. Round | 16/06/2019 | Portland Timbers 2 | - | Fresno FC | 2:2 | ||||
| 4. Round | 23/06/2019 | Orange County SC | - | Portland Timbers 2 | 0:2 | ||||
| 4. Round | 30/06/2019 | Phoenix Rising | - | Portland Timbers 2 | 4:2 | ||||
| 5. Round | 07/07/2019 | Portland Timbers 2 | - | Tulsa Roughnecks | 1:1 | ||||
| 5. Round | 21/07/2019 | Fresno FC | - | Portland Timbers 2 | 2:1 | ||||
| 6. Round | 08/08/2019 | Colorado Springs Switchbacks | - | Portland Timbers 2 | 2:2 | ||||
| 6. Round | 12/08/2019 | Portland Timbers 2 | - | New Mexico United | 3:2 | ||||
| 6. Round | 17/08/2019 | Portland Timbers 2 | - | OKC Energy FC | 2:4 | ||||
| 6. Round | 25/08/2019 | Las Vegas Lights FC | - | Portland Timbers 2 | 1:0 | ||||
| 7. Round | 01/09/2019 | Reno 1868 FC | - | Portland Timbers 2 | 1:3 | ||||
| 7. Round | 21/09/2019 | Portland Timbers 2 | - | Tacoma Defiance | 6:3 | ||||
| 8. Round | 12/10/2019 | Portland Timbers 2 | - | San Antonio FC | 3:4 |
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