| 1. Round | 06/08/1999 | Newell's Old Boys | - | San Lorenzo | 1:2 | ||||
| 2. Round | 14/08/1999 | Instituto de Córdoba | - | Newell's Old Boys | 1:1 | ||||
| 3. Round | 21/08/1999 | Newell's Old Boys | - | Rosario Central | 1:1 | ||||
| 4. Round | 28/08/1999 | Colón de Santa Fe | - | Newell's Old Boys | 2:0 | ||||
| 5. Round | 05/09/1999 | Newell's Old Boys | - | Estudiantes | 4:1 | ||||
| 6. Round | 11/09/1999 | Belgrano de Córdoba | - | Newell's Old Boys | 0:0 | ||||
| 9. Round | 02/10/1999 | Newell's Old Boys | - | Argentinos Juniors | 0:2 | ||||
| 12. Round | 30/10/1999 | River Plate | - | Newell's Old Boys | 2:0 | ||||
| 13. Round | 06/11/1999 | Boca Juniors | - | Newell's Old Boys | 2:1 | ||||
| 14. Round | 13/11/1999 | Newell's Old Boys | - | Unión de Santa Fe | 1:1 | ||||
| 18. Round | 12/12/1999 | Newell's Old Boys | - | Chacarita Juniors | 4:1 | ||||
| 19. Round | 16/12/1999 | Ferro Carril Oeste | - | Newell's Old Boys | 2:4 |  |
Argentina
Italy