| 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 | ||||
| 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 | ||||
| 15. Round | 20/11/1999 | Talleres de Córdoba | - | River Plate | 1:4 |
Argentina
Italy