| 1. Jornada | 17.03.2019 | San Antonio FC | - | Portland Timbers 2 | 1:3 |  |
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| 1. Jornada | 24.03.2019 | Portland Timbers 2 | - | Las Vegas Lights FC | 3:1 | ||||
| 1. Jornada | 31.03.2019 | Los Angeles Galaxy II | - | Portland Timbers 2 | 3:2 | ||||
| 3. Jornada | 01.05.2019 | Portland Timbers 2 | - | Rio Grande Valley FC | 1:2 | |
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| 3. Jornada | 30.05.2019 | Portland Timbers 2 | - | Real Monarchs SLC | 2:1 | ||||
| 4. Jornada | 16.06.2019 | Portland Timbers 2 | - | Fresno FC | 2:2 | ||||
| 4. Jornada | 23.06.2019 | Orange County SC | - | Portland Timbers 2 | 0:2 |  |
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| 4. Jornada | 27.06.2019 | Portland Timbers 2 | - | Reno 1868 FC | 1:2 | |
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| 4. Jornada | 30.06.2019 | Phoenix Rising | - | Portland Timbers 2 | 4:2 | ||||
| 5. Jornada | 07.07.2019 | Portland Timbers 2 | - | Tulsa Roughnecks | 1:1 | ||||
| 5. Jornada | 14.07.2019 | Sacramento Republic | - | Portland Timbers 2 | 1:0 | ||||
| 5. Jornada | 21.07.2019 | Fresno FC | - | Portland Timbers 2 | 2:1 | ||||
| 5. Jornada | 29.07.2019 | Portland Timbers 2 | - | Los Angeles Galaxy II | 1:2 |
Costa Rica
