| 4. Round | 25/06/1999 | D.C. United | - | Kansas City Wizards | 3:0 | ||||
| 5. Round | 24/07/1999 | New England Revolution | - | D.C. United | 0:2 | ||||
| 7. Round | 03/09/1999 | D.C. United | - | Dallas Burn | 4:1 | ||||
| 7. Round | 09/09/1999 | Tampa Bay Mutiny | - | D.C. United | 1:2 | ||||
| 7. Round | 24/09/1999 | Los Angeles Galaxy | - | D.C. United | 0:2 |  |
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USA