| 3. Jornada | 29.05.2014 | CD Chivas | - | Portland Timbers | 0:2 |  |
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| 4. Jornada | 08.06.2014 | Real Salt Lake | - | Portland Timbers | 1:3 | ||||
| 4. Jornada | 12.06.2014 | Portland Timbers | - | FC Dallas | 2:2 | ||||
| 4. Jornada | 28.06.2014 | Portland Timbers | - | Sporting Kansas City | 0:1 | ||||
| 5. Jornada | 05.07.2014 | Los Angeles Galaxy | - | Portland Timbers | 2:2 | ||||
| 5. Jornada | 14.07.2014 | Seattle Sounders | - | Portland Timbers | 2:0 | ||||
| 5. Jornada | 19.07.2014 | Portland Timbers | - | Colorado Rapids | 2:1 | |
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| 5. Jornada | 28.07.2014 | Impact de Montréal | - | Portland Timbers | 2:3 | ||||
| 6. Jornada | 02.08.2014 | Los Angeles Galaxy | - | Portland Timbers | 3:1 | ||||
| 6. Jornada | 10.08.2014 | Portland Timbers | - | CD Chivas | 2:0 | ||||
| 6. Jornada | 17.08.2014 | New England Revolution | - | Portland Timbers | 1:1 | ||||
| 6. Jornada | 24.08.2014 | Portland Timbers | - | Seattle Sounders | 2:4 |
Estados Unidos