| 1. Jornada | 22.03.2014 | Colorado Rapids | - | Portland Timbers | 2:0 | ||||
| 1. Jornada | 30.03.2014 | FC Dallas | - | Portland Timbers | 2:1 | ||||
| 2. Jornada | 05.04.2014 | Portland Timbers | - | Seattle Sounders | 4:4 | ||||
| 2. Jornada | 13.04.2014 | Portland Timbers | - | CD Chivas | 1:1 | ||||
| 2. Jornada | 20.04.2014 | Real Salt Lake | - | Portland Timbers | 1:0 | ||||
| 3. Jornada | 11.05.2014 | Portland Timbers | - | Los Angeles Galaxy | 1:1 | ||||
| 3. Jornada | 18.05.2014 | Portland Timbers | - | Columbus Crew | 3:3 |  |
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| 6. Jornada | 31.08.2014 | Vancouver Whitecaps | - | Portland Timbers | 0:3 |  |
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| 7. Jornada | 07.09.2014 | Portland Timbers | - | San Jose Earthquakes | 3:3 | |
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| 7. Jornada | 14.09.2014 | Colorado Rapids | - | Portland Timbers | 2:2 | ||||
| 7. Jornada | 20.09.2014 | Portland Timbers | - | Vancouver Whitecaps | 3:0 | ||||
| 7. Jornada | 27.09.2014 | Toronto FC | - | Portland Timbers | 3:2 | ||||
| 8. Jornada | 05.10.2014 | San Jose Earthquakes | - | Portland Timbers | 1:2 | ||||
| 8. Jornada | 18.10.2014 | Portland Timbers | - | Real Salt Lake | 0:0 | ||||
| 8. Jornada | 26.10.2014 | FC Dallas | - | Portland Timbers | 0:2 |
Jamaica