| 1. Round | 04/03/1999 | Platense | - | San Lorenzo | 1:2 | ||||
| 2. Round | 13/03/1999 | San Lorenzo | - | Colón de Santa Fe | 3:1 | ||||
| 3. Round | 18/03/1999 | Vélez Sarsfield | - | San Lorenzo | 1:1 | ||||
| 4. Round | 27/03/1999 | San Lorenzo | - | River Plate | 2:2 | ||||
| 5. Round | 31/03/1999 | Estudiantes | - | San Lorenzo | 0:2 | ||||
| 19. Round | 19/06/1999 | San Lorenzo | - | Racing Club | 4:0 |
Paraguay