| 1. Round | 20/03/2011 | Colorado Rapids | - | Portland Timbers | 3:1 | ||||
| 1. Round | 26/03/2011 | Toronto FC | - | Portland Timbers | 2:0 | ||||
| 2. Round | 03/04/2011 | New England Revolution | - | Portland Timbers | 1:1 | ||||
| 2. Round | 15/04/2011 | Portland Timbers | - | Chicago Fire | 4:2 |  |
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| 2. Round | 17/04/2011 | Portland Timbers | - | FC Dallas | 3:2 | ||||
| 2. Round | 24/04/2011 | Los Angeles Galaxy | - | Portland Timbers | 3:0 | ||||
| 3. Round | 01/05/2011 | Portland Timbers | - | Real Salt Lake | 1:0 | |
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| 3. Round | 07/05/2011 | Portland Timbers | - | Philadelphia Union | 1:0 | ||||
| 3. Round | 15/05/2011 | Seattle Sounders | - | Portland Timbers | 1:1 | ||||
| 3. Round | 22/05/2011 | Portland Timbers | - | Columbus Crew | 1:0 | ||||
| 3. Round | 29/05/2011 | Portland Timbers | - | D.C. United | 2:3 | ||||
| 4. Round | 05/06/2011 | CD Chivas | - | Portland Timbers | 1:0 | |
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| 4. Round | 12/06/2011 | Portland Timbers | - | Colorado Rapids | 0:1 | |
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| 4. Round | 20/06/2011 | Portland Timbers | - | New York RB | 3:3 | ||||
| 4. Round | 26/06/2011 | FC Dallas | - | Portland Timbers | 4:0 | ||||
| 5. Round | 17/07/2011 | Chicago Fire | - | Portland Timbers | 0:1 | |
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| 6. Round | 07/08/2011 | San Jose Earthquakes | - | Portland Timbers | 1:1 |  |
USA