| 1. Round | 13/04/1996 | Dallas Burn | - | San Jose Clash | n.P. | ||||
| 1. Round | 27/04/1996 | Los Angeles Galaxy | - | San Jose Clash | 2:1 | ||||
| 2. Round | 03/05/1996 | New England Revolution | - | San Jose Clash | 1:2 | ||||
| 2. Round | 07/05/1996 | San Jose Clash | - | Colorado Rapids | 3:1 | ||||
| 2. Round | 11/05/1996 | San Jose Clash | - | Los Angeles Galaxy | 1:2 | ||||
| 3. Round | 31/05/1996 | San Jose Clash | - | Columbus Crew | n.P. |  |
|||
| 3. Round | 04/06/1996 | D.C. United | - | San Jose Clash | 3:1 | |
|||
| 3. Round | 07/06/1996 | Dallas Burn | - | San Jose Clash | 4:1 | ||||
| 3. Round | 15/06/1996 | MetroStars | - | San Jose Clash | 0:1 | ||||
| 4. Round | 05/07/1996 | San Jose Clash | - | New England Revolution | n.P. | ||||
| 4. Round | 23/07/1996 | San Jose Clash | - | MetroStars | 0:1 | ||||
| 4. Round | 27/07/1996 | MetroStars | - | San Jose Clash | 4:1 | ||||
| 5. Round | 17/08/1996 | Columbus Crew | - | San Jose Clash | 2:0 | ||||
| 5. Round | 21/08/1996 | San Jose Clash | - | Dallas Burn | n.P. |
Jamaica