| 3. Jornada | 01.05.2016 | Portland Timbers | - | Toronto FC | 2:1 | ||||
| 3. Jornada | 16.05.2016 | Portland Timbers | - | New York City FC | 1:2 |  |
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| 3. Jornada | 22.05.2016 | Portland Timbers | - | Vancouver Whitecaps | 4:2 | ||||
| 3. Jornada | 29.05.2016 | Chicago Fire | - | Portland Timbers | 1:1 | ||||
| 4. Jornada | 02.06.2016 | Portland Timbers | - | San Jose Earthquakes | 1:0 | ||||
| 4. Jornada | 19.06.2016 | Real Salt Lake | - | Portland Timbers | 2:2 | |
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| 4. Jornada | 27.06.2016 | Portland Timbers | - | Houston Dynamo | 3:2 | ||||
| 5. Jornada | 05.07.2016 | Colorado Rapids | - | Portland Timbers | 0:0 | ||||
| 5. Jornada | 11.07.2016 | New York RB | - | Portland Timbers | 0:0 | ||||
| 5. Jornada | 14.07.2016 | Portland Timbers | - | Impact de Montréal | 1:1 | ||||
| 5. Jornada | 17.07.2016 | Portland Timbers | - | Seattle Sounders | 3:1 | ||||
| 5. Jornada | 23.07.2016 | Portland Timbers | - | Los Angeles Galaxy | 1:2 | ||||
| 5. Jornada | 31.07.2016 | Sporting Kansas City | - | Portland Timbers | 1:0 | ||||
| 6. Jornada | 28.08.2016 | Portland Timbers | - | Seattle Sounders | 4:2 | ||||
| 7. Jornada | 11.09.2016 | Portland Timbers | - | Real Salt Lake | 1:0 | ||||
| 7. Jornada | 18.09.2016 | Portland Timbers | - | Philadelphia Union | 2:1 |
Estados Unidos