| 1. Jornada | 31.03.2019 | Los Angeles Galaxy II | - | Portland Timbers 2 | 3:2 | ||||
| 2. Jornada | 07.04.2019 | OKC Energy FC | - | Portland Timbers 2 | 2:3 |  |
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| 4. Jornada | 23.06.2019 | Orange County SC | - | Portland Timbers 2 | 0:2 | ||||
| 4. Jornada | 27.06.2019 | Portland Timbers 2 | - | Reno 1868 FC | 1:2 | ||||
| 5. Jornada | 07.07.2019 | Portland Timbers 2 | - | Tulsa Roughnecks | 1:1 | ||||
| 5. Jornada | 14.07.2019 | Sacramento Republic | - | Portland Timbers 2 | 1:0 |  |
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| 5. Jornada | 21.07.2019 | Fresno FC | - | Portland Timbers 2 | 2:1 | ||||
| 6. Jornada | 17.08.2019 | Portland Timbers 2 | - | OKC Energy FC | 2:4 | ||||
| 6. Jornada | 25.08.2019 | Las Vegas Lights FC | - | Portland Timbers 2 | 1:0 | ||||
| 7. Jornada | 01.09.2019 | Reno 1868 FC | - | Portland Timbers 2 | 1:3 | ||||
| 7. Jornada | 08.09.2019 | Portland Timbers 2 | - | Orange County SC | 1:2 | ||||
| 7. Jornada | 14.09.2019 | Real Monarchs SLC | - | Portland Timbers 2 | 5:1 | ||||
| 8. Jornada | 12.10.2019 | Portland Timbers 2 | - | San Antonio FC | 3:4 | ||||
| 8. Jornada | 16.10.2019 | El Paso Locomotive | - | Portland Timbers 2 | 4:1 | |
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| 8. Jornada | 19.10.2019 | Rio Grande Valley FC | - | Portland Timbers 2 | 2:1 |
Estados Unidos