| 3. Round | 01/05/2016 | Portland Timbers | - | Toronto FC | 2:1 | ||||
| 3. Round | 16/05/2016 | Portland Timbers | - | New York City FC | 1:2 |  |
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| 3. Round | 22/05/2016 | Portland Timbers | - | Vancouver Whitecaps | 4:2 | ||||
| 3. Round | 29/05/2016 | Chicago Fire | - | Portland Timbers | 1:1 | ||||
| 4. Round | 02/06/2016 | Portland Timbers | - | San Jose Earthquakes | 1:0 | ||||
| 4. Round | 19/06/2016 | Real Salt Lake | - | Portland Timbers | 2:2 | |
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| 4. Round | 26/06/2016 | Portland Timbers | - | Houston Dynamo | 3:2 | ||||
| 5. Round | 05/07/2016 | Colorado Rapids | - | Portland Timbers | 0:0 | ||||
| 5. Round | 10/07/2016 | New York RB | - | Portland Timbers | 0:0 | ||||
| 5. Round | 14/07/2016 | Portland Timbers | - | Impact de Montréal | 1:1 | ||||
| 5. Round | 17/07/2016 | Portland Timbers | - | Seattle Sounders | 3:1 | ||||
| 5. Round | 23/07/2016 | Portland Timbers | - | Los Angeles Galaxy | 1:2 | ||||
| 5. Round | 31/07/2016 | Sporting Kansas City | - | Portland Timbers | 1:0 | ||||
| 6. Round | 28/08/2016 | Portland Timbers | - | Seattle Sounders | 4:2 | ||||
| 7. Round | 11/09/2016 | Portland Timbers | - | Real Salt Lake | 1:0 | ||||
| 7. Round | 17/09/2016 | Portland Timbers | - | Philadelphia Union | 2:1 |
USA