| 4. Round | 11/06/1999 | Los Angeles Galaxy | - | Chicago Fire | 2:1 | ||||
| 4. Round | 18/06/1999 | D.C. United | - | Los Angeles Galaxy | 1:2 | ||||
| 5. Round | 24/07/1999 | Los Angeles Galaxy | - | Kansas City Wizards | 2:1 | ||||
| 5. Round | 27/07/1999 | Colorado Rapids | - | Los Angeles Galaxy | 1:0 | ||||
| 5. Round | 30/07/1999 | Chicago Fire | - | Los Angeles Galaxy | 0:1 | ||||
| 6. Round | 06/08/1999 | San Jose Clash | - | Los Angeles Galaxy | 1:4 |  |
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| 7. Round | 17/09/1999 | Colorado Rapids | - | Los Angeles Galaxy | 1:0 | ||||
| 7. Round | 28/09/1999 | Los Angeles Galaxy | - | Colorado Rapids | 4:0 | |
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| 8. Round | 08/10/1999 | Kansas City Wizards | - | Los Angeles Galaxy | 0:1 |  |
USA