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| Last 50 games | more | |||
| 05.09.2008 | D2 USL1 | Portland Timbers | Miami FC |  |
| 07.09.2008 | D2 USL1 | Rochester Raging Rhinos | Portland Timbers | |
| 09.09.2008 | D2 USL1 | Montreal Impact | Portland Timbers | |
| 12.09.2008 | D2 USL1 | Portland Timbers | Charleston Battery | |
| 21.09.2008 | D2 USL1 | Carolina Railhawks | Portland Timbers | |