| 3. Round | 23/05/2008 | San Jose Earthquakes | - | Houston Dynamo | 2:1 | ||||
| 4. Round | 01/06/2008 | Real Salt Lake | - | San Jose Earthquakes | 3:1 | ||||
| 4. Round | 08/06/2008 | Columbus Crew | - | San Jose Earthquakes | 0:2 | ||||
| 5. Round | 27/07/2008 | San Jose Earthquakes | - | New York RB | 1:1 | ||||
| 6. Round | 03/08/2008 | San Jose Earthquakes | - | Los Angeles Galaxy | 3:2 | ||||
| 6. Round | 31/08/2008 | San Jose Earthquakes | - | Kansas City Wizards | 2:1 | ||||
| 7. Round | 07/09/2008 | San Jose Earthquakes | - | D.C. United | 2:1 | ||||
| 8. Round | 03/10/2008 | FC Dallas | - | San Jose Earthquakes | 1:1 | ||||
| 8. Round | 12/10/2008 | San Jose Earthquakes | - | CD Chivas | 0:1 |  |
USA
North Macedonia