| 1. Round | 05/08/1999 | River Plate | - | Instituto de Córdoba | 4:1 | ||||
| 2. Round | 14/08/1999 | Rosario Central | - | River Plate | 1:2 | ||||
| 3. Round | 23/08/1999 | River Plate | - | Colón de Santa Fe | 2:2 | ||||
| 4. Round | 27/08/1999 | Estudiantes | - | River Plate | 1:4 | ||||
| 5. Round | 04/09/1999 | River Plate | - | Belgrano de Córdoba | 4:3 | ||||
| 6. Round | 11/09/1999 | Independiente | - | River Plate | 1:1 | ||||
| 7. Round | 16/09/1999 | River Plate | - | Lanús | 3:1 |  |
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| 8. Round | 25/09/1999 | Argentinos Juniors | - | River Plate | 2:0 | ||||
| 9. Round | 02/10/1999 | River Plate | - | Vélez Sarsfield | 0:0 | ||||
| 11. Round | 16/10/1999 | River Plate | - | Boca Juniors | 2:0 | ||||
| 13. Round | 06/11/1999 | Unión de Santa Fe | - | River Plate | 1:2 | ||||
| 14. Round | 13/11/1999 | River Plate | - | Gimnasia de La Plata | 2:0 |  |
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| 15. Round | 20/11/1999 | Talleres de Córdoba | - | River Plate | 1:4 | ||||
| 16. Round | 27/11/1999 | River Plate | - | Racing Club | 1:0 | ||||
| 17. Round | 04/12/1999 | Chacarita Juniors | - | River Plate | 4:4 | ||||
| 18. Round | 11/12/1999 | River Plate | - | Ferro Carril Oeste | 4:1 | ||||
| 19. Round | 18/12/1999 | San Lorenzo | - | River Plate | 2:2 |
Colombia