| 2. Round | 13/03/1999 | River Plate | - | Argentinos Juniors | 2:0 | ||||
| 5. Round | 30/03/1999 | River Plate | - | Talleres de Córdoba | 3:0 | ||||
| 7. Round | 10/04/1999 | River Plate | - | Independiente | 2:1 | ||||
| 8. Round | 17/04/1999 | Lanús | - | River Plate | 1:1 | ||||
| 9. Round | 24/04/1999 | River Plate | - | Unión de Santa Fe | 1:0 | ||||
| 10. Round | 27/04/1999 | Ferro Carril Oeste | - | River Plate | 2:2 | ||||
| 11. Round | 01/05/1999 | River Plate | - | Gimnasia de Jujuy | 8:0 | ||||
| 15. Round | 29/05/1999 | River Plate | - | Belgrano de Córdoba | 1:0 | ||||
| 16. Round | 01/06/1999 | Newell's Old Boys | - | River Plate | 3:1 | ||||
| 17. Round | 05/06/1999 | River Plate | - | Racing Club | 2:3 | ||||
| 18. Round | 12/06/1999 | Platense | - | River Plate | 0:3 | ||||
| 19. Round | 19/06/1999 | River Plate | - | Colón de Santa Fe | 1:1 |
Paraguay