1. Round | 19/04/2021 | Vancouver Whitecaps | - | Portland Timbers | 1:0 | ||||
1. Round | 25/04/2021 | Portland Timbers | - | Houston Dynamo | 2:1 | ||||
2. Round | 02/05/2021 | FC Dallas | - | Portland Timbers | 4:1 | ||||
2. Round | 09/05/2021 | Portland Timbers | - | Seattle Sounders | 1:2 | ||||
2. Round | 16/05/2021 | San Jose Earthquakes | - | Portland Timbers | 0:2 | ||||
2. Round | 22/05/2021 | Portland Timbers | - | Los Angeles Galaxy | 3:0 | ||||
2. Round | 31/05/2021 | Philadelphia Union | - | Portland Timbers | 3:0 | ||||
3. Round | 20/06/2021 | Portland Timbers | - | Sporting Kansas City | 2:1 | ||||
3. Round | 24/06/2021 | Houston Dynamo | - | Portland Timbers | 2:2 | ||||
3. Round | 27/06/2021 | Portland Timbers | - | Minnesota United FC | 0:1 | ||||
4. Round | 02/07/2021 | Austin FC | - | Portland Timbers | 4:1 | ||||
5. Round | 05/08/2021 | Portland Timbers | - | San Jose Earthquakes | 1:1 | ||||
5. Round | 22/08/2021 | Austin FC | - | Portland Timbers | 3:1 | ||||
5. Round | 30/08/2021 | Seattle Sounders | - | Portland Timbers | 0:2 |