 |
 |
|
|
| 1st(1st leg) | Club Olimpia | - | Peñarol | 1:0 | ||
| 2nd (2nd leg) | Peñarol | - | Club Olimpia | 3:0 | ||
| 1st(1st leg): 20/10/1999 | 2nd (2nd leg): 27/10/1999 | Winner: Peñarol | ||||
| 1st(1st leg) | San Lorenzo | - | Corinthians SP | 2:1 | ||
| 2nd (2nd leg) | Corinthians SP | - | San Lorenzo | 1:2 | ||
| 1st(1st leg): 21/10/1999 | 2nd (2nd leg): 27/10/1999 | Winner: San Lorenzo | ||||
| 1st(1st leg) | Palmeiras | - | Cruzeiro | 7:3 | ||
| 2nd (2nd leg) | Cruzeiro | - | Palmeiras | 2:0 | ||
| 1st(1st leg): 22/10/1999 | 2nd (2nd leg): 29/10/1999 | Winner: Palmeiras | ||||
| 1st(1st leg) | Independiente | - | Flamengo RJ | 1:1 | ||
| 2nd (2nd leg) | Flamengo RJ | - | Independiente | 4:0 | ||
| 1st(1st leg): 02/11/1999 | 2nd (2nd leg): 05/11/1999 | Winner: Flamengo RJ | ||||
