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| 1st(1st leg) | Cerro Porteño | - | Nacional | 5:0 (3:0) | ||
| 2nd (2nd leg) | Nacional | - | Cerro Porteño | 2:1 (1:0) | ||
| 1st(1st leg): 14/04/1999 | 2nd (2nd leg): 21/04/1999 | Winner: Cerro Porteño | ||||
| 1st(1st leg) | Universitario de Deportes | - | Vélez Sarsfield | 0:0 (0:0) | ||
| 2nd (2nd leg) | Vélez Sarsfield | - | Universitario de Deportes | 4:0 (2:0) | ||
| 1st(1st leg): 14/04/1999 | 2nd (2nd leg): 21/04/1999 | Winner: Vélez Sarsfield | ||||
| 1st(1st leg) | Jorge Wilstermann | - | Corinthians SP | 1:1 (0:0) | ||
| 2nd (2nd leg) | Corinthians SP | - | Jorge Wilstermann | 5:2 (2:0) | ||
| 1st(1st leg): 14/04/1999 | 2nd (2nd leg): 21/04/1999 | Winner: Corinthians SP | ||||
| 1st(1st leg) | Bella Vista | - | Universidad Católica | 2:2 (0:1) | ||
| 2nd (2nd leg) | Universidad Católica | - | Bella Vista | 1:3 (0:2) | ||
| 1st(1st leg): 14/04/1999 | 2nd (2nd leg): 20/04/1999 | Winner: Bella Vista | ||||
| 1st(1st leg) | River Plate | - | LDU Quito | 1:0 (1:0) | ||
| 2nd (2nd leg) | LDU Quito | - | River Plate | 4:5 (0:0, 1:0, 1:0) pso | ||
| 1st(1st leg): 14/04/1999 | 2nd (2nd leg): 21/04/1999 | Winner: River Plate | ||||
| 1st(1st leg) | Emelec | - | Estudiantes de Mérida | 1:3 (1:3) | ||
| 2nd (2nd leg) | Estudiantes de Mérida | - | Emelec | 0:1 (0:1) | ||
| 1st(1st leg): 14/04/1999 | 2nd (2nd leg): 21/04/1999 | Winner: Estudiantes de Mérida | ||||
| 1st(1st leg) | Deportivo Cali | - | Colo-Colo | 2:0 (2:0) | ||
| 2nd (2nd leg) | Colo-Colo | - | Deportivo Cali | 1:0 (0:0) | ||
| 1st(1st leg): 14/04/1999 | 2nd (2nd leg): 21/04/1999 | Winner: Deportivo Cali | ||||
| 1st(1st leg) | Palmeiras | - | Vasco da Gama - RJ | 1:1 (1:0) | ||
| 2nd (2nd leg) | Vasco da Gama - RJ | - | Palmeiras | 2:4 (2:2) | ||
| 1st(1st leg): 14/04/1999 | 2nd (2nd leg): 21/04/1999 | Winner: Palmeiras | ||||
