| 1. Round | 25/03/2017 | Columbus Crew | - | Portland Timbers | 3:2 | ||||
| 2. Round | 09/04/2017 | Philadelphia Union | - | Portland Timbers | 1:3 | ||||
| 2. Round | 22/04/2017 | Portland Timbers | - | Vancouver Whitecaps | 2:1 |  |
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| 2. Round | 30/04/2017 | FC Dallas | - | Portland Timbers | 2:2 | ||||
| 3. Round | 07/05/2017 | San Jose Earthquakes | - | Portland Timbers | 3:0 | ||||
| 3. Round | 27/05/2017 | Seattle Sounders | - | Portland Timbers | 1:0 | ||||
| 5. Round | 20/07/2017 | Portland Timbers | - | Real Salt Lake | 1:4 |  |
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| 5. Round | 23/07/2017 | Vancouver Whitecaps | - | Portland Timbers | 1:2 | |
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| 7. Round | 09/09/2017 | New York City FC | - | Portland Timbers | 0:1 | ||||
| 7. Round | 25/09/2017 | Portland Timbers | - | Orlando City | 3:0 |
England