| 6. Journée | 08.08.2019 | Colorado Springs Switchbacks | - | Portland Timbers 2 | 2:2 | ||||
| 6. Journée | 12.08.2019 | Portland Timbers 2 | - | New Mexico United | 3:2 | ||||
| 6. Journée | 17.08.2019 | Portland Timbers 2 | - | OKC Energy FC | 2:4 | ||||
| 6. Journée | 25.08.2019 | Las Vegas Lights FC | - | Portland Timbers 2 | 1:0 | ||||
| 7. Journée | 01.09.2019 | Reno 1868 FC | - | Portland Timbers 2 | 1:3 |  |
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| 7. Journée | 14.09.2019 | Real Monarchs SLC | - | Portland Timbers 2 | 5:1 | ||||
| 7. Journée | 21.09.2019 | Portland Timbers 2 | - | Tacoma Defiance | 6:3 | ||||
| 8. Journée | 06.10.2019 | Portland Timbers 2 | - | Phoenix Rising | 3:5 |
États-Unis