| 5. Round | 16/08/2021 | Portland Timbers | - | Seattle Sounders | 2:6 | ||||
| 5. Round | 22/08/2021 | Austin FC | - | Portland Timbers | 3:1 | ||||
| 6. Round | 16/09/2021 | Portland Timbers | - | Colorado Rapids | 2:2 | ||||
| 6. Round | 20/09/2021 | Portland Timbers | - | Los Angeles FC | 2:1 | ||||
| 6. Round | 26/09/2021 | Portland Timbers | - | Real Salt Lake | 6:1 |  |
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| 6. Round | 30/09/2021 | Los Angeles FC | - | Portland Timbers | 1:2 | ||||
| 7. Round | 03/10/2021 | Portland Timbers | - | Inter Miami CF | 1:0 | |
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| 7. Round | 17/10/2021 | Los Angeles Galaxy | - | Portland Timbers | 2:1 | ||||
| 7. Round | 21/10/2021 | Portland Timbers | - | Vancouver Whitecaps | 2:3 | ||||
| 7. Round | 24/10/2021 | Colorado Rapids | - | Portland Timbers | 2:0 | ||||
| 7. Round | 28/10/2021 | Portland Timbers | - | San Jose Earthquakes | 2:0 | ||||
| 8. Round | 04/11/2021 | Real Salt Lake | - | Portland Timbers | 1:3 | ||||
| 8. Round | 07/11/2021 | Portland Timbers | - | Austin FC | 3:0 | |
Poland