| 1. Round | 31/03/2019 | Los Angeles Galaxy II | - | Portland Timbers 2 | 3:2 | ||||
| 2. Round | 07/04/2019 | OKC Energy FC | - | Portland Timbers 2 | 2:3 |  |
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| 4. Round | 23/06/2019 | Orange County SC | - | Portland Timbers 2 | 0:2 | ||||
| 4. Round | 27/06/2019 | Portland Timbers 2 | - | Reno 1868 FC | 1:2 | ||||
| 5. Round | 07/07/2019 | Portland Timbers 2 | - | Tulsa Roughnecks | 1:1 | ||||
| 5. Round | 14/07/2019 | Sacramento Republic | - | Portland Timbers 2 | 1:0 |  |
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| 5. Round | 21/07/2019 | Fresno FC | - | Portland Timbers 2 | 2:1 | ||||
| 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 | 08/09/2019 | Portland Timbers 2 | - | Orange County SC | 1:2 | ||||
| 7. Round | 14/09/2019 | Real Monarchs SLC | - | Portland Timbers 2 | 5:1 | ||||
| 8. Round | 12/10/2019 | Portland Timbers 2 | - | San Antonio FC | 3:4 | ||||
| 8. Round | 16/10/2019 | El Paso Locomotive | - | Portland Timbers 2 | 4:1 | |
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| 8. Round | 19/10/2019 | Rio Grande Valley FC | - | Portland Timbers 2 | 2:1 |
USA