| 1. Round | 06/08/1999 | Newell's Old Boys | - | San Lorenzo | 1:2 |  |
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| 2. Round | 12/08/1999 | San Lorenzo | - | Unión de Santa Fe | 3:1 | ||||
| 3. Round | 20/08/1999 | Gimnasia de La Plata | - | San Lorenzo | 1:2 | ||||
| 4. Round | 28/08/1999 | San Lorenzo | - | Talleres de Córdoba | 1:0 | ||||
| 5. Round | 04/09/1999 | Racing Club | - | San Lorenzo | 1:1 | ||||
| 6. Round | 09/09/1999 | San Lorenzo | - | Chacarita Juniors | 3:1 | ||||
| 7. Round | 18/09/1999 | Ferro Carril Oeste | - | San Lorenzo | 0:0 |  |
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| 9. Round | 02/10/1999 | San Lorenzo | - | Instituto de Córdoba | 2:0 | ||||
| 10. Round | 09/10/1999 | Rosario Central | - | San Lorenzo | 3:1 | ||||
| 11. Round | 14/10/1999 | San Lorenzo | - | Colón de Santa Fe | 5:1 | ||||
| 12. Round | 30/10/1999 | Estudiantes | - | San Lorenzo | 3:2 | ||||
| 13. Round | 06/11/1999 | San Lorenzo | - | Belgrano de Córdoba | 1:0 | ||||
| 14. Round | 13/11/1999 | Independiente | - | San Lorenzo | 0:3 | ||||
| 16. Round | 27/11/1999 | Argentinos Juniors | - | San Lorenzo | 0:0 | ||||
| 17. Round | 02/12/1999 | San Lorenzo | - | Vélez Sarsfield | 2:0 |
Argentina