| 5. Round | 26/07/2009 | San Jose Earthquakes | - | D.C. United | 2:2 | ||||
| 6. Round | 02/08/2009 | San Jose Earthquakes | - | Seattle Sounders | 4:0 | ||||
| 6. Round | 09/08/2009 | San Jose Earthquakes | - | Columbus Crew | 0:3 | ||||
| 6. Round | 30/08/2009 | New England Revolution | - | San Jose Earthquakes | 2:1 |  |
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| 7. Round | 19/09/2009 | San Jose Earthquakes | - | Colorado Rapids | 1:1 | ||||
| 7. Round | 24/09/2009 | Colorado Rapids | - | San Jose Earthquakes | 1:1 | ||||
| 7. Round | 27/09/2009 | D.C. United | - | San Jose Earthquakes | 1:2 | |
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| 8. Round | 04/10/2009 | San Jose Earthquakes | - | New York RB | 1:0 | ||||
| 8. Round | 18/10/2009 | CD Chivas | - | San Jose Earthquakes | 2:2 | ||||
| 8. Round | 25/10/2009 | Los Angeles Galaxy | - | San Jose Earthquakes | 2:0 |
El Salvador