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| Last 10 games | more | |||
| 04.07.2008 | CF Club Friendly | Portland Timbers | Morelia | 0-2 |
| 29.06.2008 | D2 USL1 | Atlanta Silverbacks | Portland Timbers | 0-2 |
| 28.06.2008 | D2 USL1 | Carolina Railhawks | Portland Timbers | 1-0 |
| 13.06.2008 | D2 USL1 | Portland Timbers | Atlanta Silverbacks | 2-2 |
| 11.06.2008 | Cup Round 1 | Portland Timbers | Hollywood United | 2-3 |
| 08.06.2008 | D2 USL1 | Vancouver Whitecaps | Portland Timbers | 3-1 |
| 06.06.2008 | D2 USL1 | Portland Timbers | Minnesota Thunder | 0-0 |
| 02.06.2008 | D2 USL1 | Rochester Raging Rhinos | Portland Timbers | 2-1 |
| 31.05.2008 | D2 USL1 | Montreal Impact | Portland Timbers | 0-1 |
| 26.05.2008 | D2 USL1 | Portland Timbers | Miami FC | 0-2 |
| Next 10 games | more | |||
| 11.07.2008 | D2 USL1 | Portland Timbers | Puerto Rico Islanders |  |
| 16.07.2008 | CF Club Friendly | Portland Timbers | Tigres | |
| 19.07.2008 | D2 USL1 | Atlanta Silverbacks | Portland Timbers | |
| 20.07.2008 | D2 USL1 | Charleston Battery | Portland Timbers | |
| 25.07.2008 | D2 USL1 | Portland Timbers | Carolina Railhawks | |
| 03.08.2008 | D2 USL1 | Minnesota Thunder | Portland Timbers | |
| 08.08.2008 | D2 USL1 | Portland Timbers | Seattle Sounders | |
| 10.08.2008 | D2 USL1 | Portland Timbers | Charleston Battery | |
| 17.08.2008 | D2 USL1 | Portland Timbers | Montreal Impact | |
| 23.08.2008 | D2 USL1 | Vancouver Whitecaps | Portland Timbers | |