| 1. Journée | 09.03.2014 | Portland Timbers | - | Philadelphia Union | 1:1 | ||||
| 1. Journée | 30.03.2014 | FC Dallas | - | Portland Timbers | 2:1 |  |
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| 2. Journée | 05.04.2014 | Portland Timbers | - | Seattle Sounders | 4:4 | ||||
| 2. Journée | 13.04.2014 | Portland Timbers | - | CD Chivas | 1:1 | ||||
| 2. Journée | 20.04.2014 | Real Salt Lake | - | Portland Timbers | 1:0 | ||||
| 2. Journée | 27.04.2014 | Houston Dynamo | - | Portland Timbers | 1:1 | ||||
| 3. Journée | 04.05.2014 | Portland Timbers | - | D.C. United | 3:2 | ||||
| 3. Journée | 29.05.2014 | CD Chivas | - | Portland Timbers | 0:2 | ||||
| 4. Journée | 02.06.2014 | Portland Timbers | - | Vancouver Whitecaps | 3:4 | ||||
| 4. Journée | 08.06.2014 | Real Salt Lake | - | Portland Timbers | 1:3 | ||||
| 5. Journée | 05.07.2014 | Los Angeles Galaxy | - | Portland Timbers | 2:2 | ||||
| 5. Journée | 14.07.2014 | Seattle Sounders | - | Portland Timbers | 2:0 | ||||
| 6. Journée | 02.08.2014 | Los Angeles Galaxy | - | Portland Timbers | 3:1 | ||||
| 7. Journée | 07.09.2014 | Portland Timbers | - | San Jose Earthquakes | 3:3 |  |
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| 7. Journée | 14.09.2014 | Colorado Rapids | - | Portland Timbers | 2:2 |
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