| 1. Round | 23/03/2014 | Sporting Kansas City | - | San Jose Earthquakes | 1:0 | ||||
| 1. Round | 30/03/2014 | San Jose Earthquakes | - | New England Revolution | 1:2 | ||||
| 2. Round | 13/04/2014 | San Jose Earthquakes | - | Columbus Crew | 1:1 | ||||
| 2. Round | 19/04/2014 | Colorado Rapids | - | San Jose Earthquakes | 0:0 | ||||
| 2. Round | 27/04/2014 | San Jose Earthquakes | - | CD Chivas | 1:0 | ||||
| 3. Round | 04/05/2014 | Vancouver Whitecaps | - | San Jose Earthquakes | 3:2 | ||||
| 3. Round | 11/05/2014 | San Jose Earthquakes | - | FC Dallas | 2:1 | ||||
| 3. Round | 01/06/2014 | FC Dallas | - | San Jose Earthquakes | 1:2 | ||||
| 4. Round | 07/06/2014 | Toronto FC | - | San Jose Earthquakes | 1:0 |  |
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| 5. Round | 12/07/2014 | San Jose Earthquakes | - | D.C. United | 1:2 |
USA