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| Last 10 games | more | |||
| 21.09.2008 | D2 USL1 | Carolina Railhawks | Portland Timbers | 1-0 |
| 12.09.2008 | D2 USL1 | Portland Timbers | Charleston Battery | 1-2 |
| 09.09.2008 | D2 USL1 | Montreal Impact | Portland Timbers | 2-0 |
| 07.09.2008 | D2 USL1 | Rochester Raging Rhinos | Portland Timbers | 2-0 |
| 05.09.2008 | D2 USL1 | Portland Timbers | Miami FC | 4-0 |
| 23.08.2008 | D2 USL1 | Vancouver Whitecaps | Portland Timbers | 2-1 |
| 17.08.2008 | D2 USL1 | Portland Timbers | Montreal Impact | 2-1 |
| 10.08.2008 | D2 USL1 | Portland Timbers | Charleston Battery | 1-1 |
| 08.08.2008 | D2 USL1 | Portland Timbers | Seattle Sounders | 0-1 |
| 03.08.2008 | D2 USL1 | Minnesota Thunder | Portland Timbers | 2-2 |