| 2. Jornada | 02.05.2021 | FC Dallas | - | Portland Timbers | 4:1 | ||||
| 2. Jornada | 16.05.2021 | San Jose Earthquakes | - | Portland Timbers | 0:2 | ||||
| 2. Jornada | 22.05.2021 | Portland Timbers | - | Los Angeles Galaxy | 3:0 | ||||
| 2. Jornada | 31.05.2021 | Philadelphia Union | - | Portland Timbers | 3:0 | ||||
| 3. Jornada | 20.06.2021 | Portland Timbers | - | Sporting Kansas City | 2:1 |  |
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| 3. Jornada | 24.06.2021 | Houston Dynamo | - | Portland Timbers | 2:2 | ||||
| 3. Jornada | 27.06.2021 | Portland Timbers | - | Minnesota United FC | 0:1 | ||||
| 4. Jornada | 02.07.2021 | Austin FC | - | Portland Timbers | 4:1 | ||||
| 4. Jornada | 18.07.2021 | Portland Timbers | - | FC Dallas | 1:0 | ||||
| 4. Jornada | 25.07.2021 | Minnesota United FC | - | Portland Timbers | 2:1 | ||||
| 5. Jornada | 19.08.2021 | Sporting Kansas City | - | Portland Timbers | 1:1 | ||||
| 6. Jornada | 04.09.2021 | Houston Dynamo | - | Portland Timbers | 0:2 | |
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| 7. Jornada | 24.10.2021 | Colorado Rapids | - | Portland Timbers | 2:0 | ||||
| 8. Jornada | 08.11.2021 | Portland Timbers | - | Austin FC | 3:0 |
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