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| Last 50 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 | |
| 28.08.2008 | D2 USL1 | Montreal Impact | Portland Timbers | |
| 05.09.2008 | D2 USL1 | Portland Timbers | Miami FC | |
| 07.09.2008 | D2 USL1 | Rochester Raging Rhinos | Portland Timbers | |
| 12.09.2008 | D2 USL1 | Portland Timbers | Charleston Battery | |
| 21.09.2008 | D2 USL1 | Carolina Railhawks | Portland Timbers | |