| 3. Jornada | 28.05.2009 | Columbus Crew | - | San Jose Earthquakes | 2:1 | ||||
| 3. Jornada | 31.05.2009 | San Jose Earthquakes | - | Real Salt Lake | 2:1 |  |
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| 5. Jornada | 04.07.2009 | Real Salt Lake | - | San Jose Earthquakes | 1:1 | ||||
| 5. Jornada | 12.07.2009 | San Jose Earthquakes | - | Toronto FC | 1:3 | ||||
| 5. Jornada | 19.07.2009 | Chicago Fire | - | San Jose Earthquakes | 2:0 | ||||
| 5. Jornada | 26.07.2009 | San Jose Earthquakes | - | D.C. United | 2:2 | |
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| 6. Jornada | 02.08.2009 | San Jose Earthquakes | - | Seattle Sounders | 4:0 | |
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| 6. Jornada | 09.08.2009 | San Jose Earthquakes | - | Columbus Crew | 0:3 | ||||
| 6. Jornada | 23.08.2009 | San Jose Earthquakes | - | Kansas City Wizards | 1:0 | ||||
| 7. Jornada | 19.09.2009 | San Jose Earthquakes | - | Colorado Rapids | 1:1 | ||||
| 8. Jornada | 08.10.2009 | San Jose Earthquakes | - | FC Dallas | 1:2 | ||||
| 8. Jornada | 10.10.2009 | Toronto FC | - | San Jose Earthquakes | 1:1 | |
Trinidad y Tobago