| Quarter-finals | 15/10/1999 | D.C. United | - | Miami Fusion | 2:0 | ||||
| Quarter-finals | 23/10/1999 | Miami Fusion | - | D.C. United | n.P. | ||||
| Semi-finals | 30/10/1999 | D.C. United | - | Columbus Crew | 2:1 | ||||
| Semi-finals | 06/11/1999 | Columbus Crew | - | D.C. United | 5:1 | ||||
| Final | 20/11/1999 | Los Angeles Galaxy | - | D.C. United | 0:2 |  |
Argentina