| 2. Jornada | 19.07.2020 | Tacoma Defiance | - | Portland Timbers 2 | 3:0 |  |
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| 2. Jornada | 30.07.2020 | Portland Timbers 2 | - | Reno 1868 FC | 1:4 | ||||
| 3. Jornada | 27.08.2020 | Portland Timbers 2 | - | Los Angeles Galaxy II | 2:3 | ||||
| 4. Jornada | 02.09.2020 | Portland Timbers 2 | - | Sacramento Republic | 1:2 |  |
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| 4. Jornada | 06.09.2020 | Reno 1868 FC | - | Portland Timbers 2 | 7:1 | |
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| 4. Jornada | 10.09.2020 | Portland Timbers 2 | - | Tacoma Defiance | 3:0 | ||||
| 4. Jornada | 17.09.2020 | Real Monarchs SLC | - | Portland Timbers 2 | 1:2 | ||||
| 4. Jornada | 21.09.2020 | Portland Timbers 2 | - | Reno 1868 FC | 2:5 | ||||
| 4. Jornada | 25.09.2020 | Portland Timbers 2 | - | Tacoma Defiance | 3:1 | ||||
| 4. Jornada | 27.09.2020 | Tacoma Defiance | - | Portland Timbers 2 | 2:1 | ||||
| 5. Jornada | 04.10.2020 | Sacramento Republic | - | Portland Timbers 2 | 4:0 |
Estados Unidos