| date | season | team | score | team | venue | referee | att. | sources |
|---|---|---|---|---|---|---|---|---|
| Oct. 3, 1999 | 1999 | Chicago Fire | 2 - 2 | D.C. United | Soldier Field | 9763 | 1 | |
| Oct. 1, 1999 | 1999 | Alajuelense | 1 - 1 | Chicago Fire | Estadío Alejandro Morera Soto | 8183 | 1 | |
| Oct. 1, 1999 | 1999 | D.C. United | 1 - 3 | Necaxa | Aguascalientes, Mexico | 8183 | 1 | |
| Sept. 29, 1999 | 1999 | Chicago Fire | 2 - 0 | Joe Public F.C. | Soldier Field | 6521 | 1 | |
| Sept. 29, 1999 | 1999 | D.C. United | 1 - 0 | Olimpia | RFK Stadium | 7127 | 1 | |
| Aug. 18, 1999 | 1999 | Los Angeles Galaxy | 1 - 1 | Necaxa | Rose Bowl | 10019 | 1 |