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| U | River Plate | - | Vélez Sarsfield | 2:0 (1:0) | ||
| R | Vélez Sarsfield | - | River Plate | 1:0 (0:0) | ||
| U: 05.05.1999 | R: 12.05.1999 | Winnaars: River Plate | ||||
| U | Palmeiras | - | Corinthians SP | 2:0 (1:0) | ||
| R | Corinthians SP | - | Palmeiras | 2:4 (1:0, 2:0, 2:0) d.p. | ||
| U: 05.05.1999 | R: 12.05.1999 | Winnaars: Palmeiras | ||||
| U | Estudiantes de Mérida | - | Cerro Porteño | 3:0 (2:0) | ||
| R | Cerro Porteño | - | Estudiantes de Mérida | 4:0 (1:0) | ||
| U: 05.05.1999 | R: 12.05.1999 | Winnaars: Cerro Porteño | ||||
| U | Deportivo Cali | - | Bella Vista | 2:1 (1:1) | ||
| R | Bella Vista | - | Deportivo Cali | 1:1 (0:0) | ||
| U: 05.05.1999 | R: 12.05.1999 | Winnaars: Deportivo Cali | ||||
