Quarter-finals | 16/10/1999 | Columbus Crew | - | Tampa Bay Mutiny | 2:0 | ||||
Semi-finals | 30/10/1999 | D.C. United | - | Columbus Crew | 2:1 | ||||
Semi-finals | 06/11/1999 | Columbus Crew | - | D.C. United | 5:1 | ||||
Semi-finals | 12/11/1999 | D.C. United | - | Columbus Crew | 4:0 |