| 1. Round | 04/03/2017 | Portland Timbers | - | Minnesota United FC | 5:1 | ||||
| 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 | 14/05/2017 | Portland Timbers | - | Atlanta United FC | 1:1 |  |
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| 3. Round | 20/05/2017 | Impact de Montréal | - | Portland Timbers | 4:1 | ||||
| 3. Round | 27/05/2017 | Seattle Sounders | - | Portland Timbers | 1:0 | ||||
| 4. Round | 03/06/2017 | Portland Timbers | - | San Jose Earthquakes | 2:0 | ||||
| 4. Round | 11/06/2017 | Portland Timbers | - | FC Dallas | 2:0 | ||||
| 6. Round | 06/08/2017 | Portland Timbers | - | Los Angeles Galaxy | 3:1 | |
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| 7. Round | 17/09/2017 | Real Salt Lake | - | Portland Timbers | 2:1 | ||||
| 7. Round | 25/09/2017 | Portland Timbers | - | Orlando City | 3:0 | |
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| 7. Round | 01/10/2017 | San Jose Earthquakes | - | Portland Timbers | 2:1 | ||||
| 8. Round | 16/10/2017 | Portland Timbers | - | D.C. United | 4:0 | ||||
| 8. Round | 22/10/2017 | Portland Timbers | - | Vancouver Whitecaps | 2:1 | |
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England
