| 5. Jornada | 31.07.2016 | Sporting Kansas City | - | Portland Timbers | 1:0 | ||||
| 6. Jornada | 07.08.2016 | Portland Timbers | - | Sporting Kansas City | 3:0 | ||||
| 6. Jornada | 14.08.2016 | D.C. United | - | Portland Timbers | 2:0 |  |
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| 6. Jornada | 22.08.2016 | Seattle Sounders | - | Portland Timbers | 3:1 | ||||
| 6. Jornada | 28.08.2016 | Portland Timbers | - | Seattle Sounders | 4:2 |  |
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| 7. Jornada | 04.09.2016 | FC Dallas | - | Portland Timbers | 3:1 | ||||
| 7. Jornada | 11.09.2016 | Portland Timbers | - | Real Salt Lake | 1:0 | ||||
| 7. Jornada | 18.09.2016 | Portland Timbers | - | Philadelphia Union | 2:1 | ||||
| 8. Jornada | 02.10.2016 | Colorado Rapids | - | Portland Timbers | 1:0 | ||||
| 8. Jornada | 16.10.2016 | Portland Timbers | - | Colorado Rapids | 1:0 | |
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| 8. Jornada | 23.10.2016 | Vancouver Whitecaps | - | Portland Timbers | 4:1 |
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