Portland Timbers 
| 2009-04-25 | NASL | Vancouver Whitecaps FC | (A) | 0 | - 1 | L | |
| 2009-04-30 | NASL | Carolina RailHawks FC | (H) | 0 | - 0 | D | |
| 2009-05-02 | NASL | Carolina RailHawks FC | (H) | 2 | - 0 | W | |
| 2009-05-09 | NASL | Cleveland | (A) | 0 | - 0 | D | |
| 2009-05-14 | NASL | Rochester Rhinos | (H) | 2 | - 1 | W | |
| 2009-05-22 | NASL | Puerto Rico Islanders | (A) | 1 | - 1 | D | |
| 2009-05-24 | NASL | Puerto Rico Islanders | (A) | 2 | - 1 | W | |
| 2009-05-30 | NASL | Vancouver Whitecaps FC | (H) | 2 | - 0 | W | |
| 2009-06-04 | NASL | Montreal Impact | (H) | 1 | - 0 | W | |
| 2009-06-11 | NASL | Carolina RailHawks FC | (A) | 0 | - 0 | D | |
| 2009-06-13 | NASL | Charleston Battery | (A) | 1 | - 1 | D | |
| 2009-06-19 | NASL | Minnesota Thund. | (H) | 5 | - 1 | W | |
| 2009-06-28 | NASL | Montreal Impact | (H) | 4 | - 0 | W | |
| 2009-07-04 | NASL | Minnesota Thund. | (A) | 1 | - 1 | D | |
| 2009-07-11 | NASL | Austin | (A) | 2 | - 1 | W | |
| 2009-07-17 | NASL | Miami FC | (A) | 1 | - 1 | D | |
| 2009-07-19 | NASL | Miami FC | (A) | 3 | - 0 | W | |
| 2009-07-23 | NASL | Puerto Rico Islanders | (H) | 0 | - 0 | D | |
| 2009-08-01 | NASL | Minnesota Thund. | (A) | 1 | - 1 | D | |
| 2009-08-06 | NASL | Vancouver Whitecaps FC | (H) | 1 | - 0 | W | |
| 2009-08-08 | NASL | Charleston Battery | (H) | 3 | - 1 | W | |
| 2009-08-12 | NASL | Montreal Impact | (A) | 1 | - 0 | W | |
| 2009-08-15 | NASL | Rochester Rhinos | (A) | 4 | - 1 | W | |
| 2009-08-22 | NASL | Miami FC | (H) | 3 | - 1 | W | |
| 2009-08-28 | NASL | Charleston Battery | (A) | 0 | - 0 | D | |
| 2009-09-03 | NASL | Rochester Rhinos | (H) | 1 | - 2 | L | |
| 2009-09-07 | NASL | Austin | (A) | 1 | - 0 | W | |
| 2009-09-11 | NASL | Austin | (H) | 1 | - 2 | L | |
| 2009-09-13 | NASL | Cleveland | (H) | 0 | - 1 | L | |
| 2009-09-17 | NASL | Cleveland | (H) | 2 | - 1 | W |