| 1. Jornada | 24.03.2019 | Portland Timbers 2 | - | Las Vegas Lights FC | 3:1 |  |
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| 3. Jornada | 01.05.2019 | Portland Timbers 2 | - | Rio Grande Valley FC | 1:2 | ||||
| 3. Jornada | 12.05.2019 | Tacoma Defiance | - | Portland Timbers 2 | 1:4 | |
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| 3. Jornada | 26.05.2019 | Portland Timbers 2 | - | El Paso Locomotive | 1:1 | |
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| 3. Jornada | 30.05.2019 | Portland Timbers 2 | - | Real Monarchs SLC | 2:1 | |
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| 4. Jornada | 16.06.2019 | Portland Timbers 2 | - | Fresno FC | 2:2 | |
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| 5. Jornada | 29.07.2019 | Portland Timbers 2 | - | Los Angeles Galaxy II | 1:2 | |
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| 6. Jornada | 25.08.2019 | Las Vegas Lights FC | - | Portland Timbers 2 | 1:0 | ||||
| 7. Jornada | 21.09.2019 | Portland Timbers 2 | - | Tacoma Defiance | 6:3 | |
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Colombia
