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| 1st(1st leg) | River Plate | - | Vélez Sarsfield | 2:0 (1:0) | ||
| 2nd (2nd leg) | Vélez Sarsfield | - | River Plate | 1:0 (0:0) | ||
| 1st(1st leg): 05/05/1999 | 2nd (2nd leg): 12/05/1999 | Winner: River Plate | ||||
| 1st(1st leg) | Palmeiras | - | Corinthians SP | 2:0 (1:0) | ||
| 2nd (2nd leg) | Corinthians SP | - | Palmeiras | 2:4 (1:0, 2:0, 2:0) pso | ||
| 1st(1st leg): 05/05/1999 | 2nd (2nd leg): 12/05/1999 | Winner: Palmeiras | ||||
| 1st(1st leg) | Estudiantes de Mérida | - | Cerro Porteño | 3:0 (2:0) | ||
| 2nd (2nd leg) | Cerro Porteño | - | Estudiantes de Mérida | 4:0 (1:0) | ||
| 1st(1st leg): 05/05/1999 | 2nd (2nd leg): 12/05/1999 | Winner: Cerro Porteño | ||||
| 1st(1st leg) | Deportivo Cali | - | Bella Vista | 2:1 (1:1) | ||
| 2nd (2nd leg) | Bella Vista | - | Deportivo Cali | 1:1 (0:0) | ||
| 1st(1st leg): 05/05/1999 | 2nd (2nd leg): 12/05/1999 | Winner: Deportivo Cali | ||||
