series
| Sept. 9, 1999 | CMs | 1999 | E | Colo-Colo | 0 - 0 | Universidad de Chile | 1 | |
| July 28, 1999 | CMs | 1999 | E | Colo-Colo | 2 - 0 | Universidad de Chile | 1 |
scoreboard
| CMn | 1999 | A | América de Cali | 3 - 1 | CD El Nacional | 1 | |
| CMs | 1999 | A | Palmeiras | 4 - 2 | Racing Club de Avellaneda | 1 | |
| GT | 1999 | Dominica | 0 - 2 | Saint Lucia | Guyana | 2 | |
| IF | 1999 | Bermuda | 3 - 1 | Cayman Islands | Bermuda | 2 |