| 5. Round | 24/07/2011 | Columbus Crew | - | Portland Timbers | 1:0 | ||||
| 5. Round | 31/07/2011 | Portland Timbers | - | Toronto FC | 2:2 | ||||
| 6. Round | 04/08/2011 | Portland Timbers | - | Los Angeles Galaxy | 3:0 | ||||
| 6. Round | 07/08/2011 | San Jose Earthquakes | - | Portland Timbers | 1:1 |  |
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| 6. Round | 15/08/2011 | Houston Dynamo | - | Portland Timbers | 2:1 | |
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| 6. Round | 21/08/2011 | Portland Timbers | - | Vancouver Whitecaps | 2:1 | ||||
| 6. Round | 25/08/2011 | Portland Timbers | - | CD Chivas | 1:0 | ||||
| 7. Round | 11/09/2011 | Philadelphia Union | - | Portland Timbers | 0:0 | ||||
| 7. Round | 17/09/2011 | Portland Timbers | - | New England Revolution | 3:0 | ||||
| 7. Round | 22/09/2011 | Portland Timbers | - | San Jose Earthquakes | 1:1 | ||||
| 7. Round | 25/09/2011 | New York RB | - | Portland Timbers | 2:0 | ||||
| 8. Round | 02/10/2011 | Vancouver Whitecaps | - | Portland Timbers | 0:1 | ||||
| 8. Round | 15/10/2011 | Portland Timbers | - | Houston Dynamo | 0:2 | ||||
| 8. Round | 20/10/2011 | D.C. United | - | Portland Timbers | 1:1 | ||||
| 8. Round | 23/10/2011 | Real Salt Lake | - | Portland Timbers | 1:1 |
Jamaica