| 1. Round | 07/08/1999 | Boca Juniors | - | Independiente | 3:0 |  |
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| 2. Round | 17/08/1999 | Boca Juniors | - | Racing Club | 1:1 | |
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| 3. Round | 21/08/1999 | Lanús | - | Boca Juniors | 1:4 | |
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| 4. Round | 28/08/1999 | Boca Juniors | - | Chacarita Juniors | 2:0 | ||||
| 5. Round | 02/09/1999 | Argentinos Juniors | - | Boca Juniors | 1:1 | |
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| 6. Round | 11/09/1999 | Boca Juniors | - | Ferro Carril Oeste | 2:0 | |
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| 7. Round | 18/09/1999 | Vélez Sarsfield | - | Boca Juniors | 3:1 |  |
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| 9. Round | 01/10/1999 | Gimnasia de Jujuy | - | Boca Juniors | 1:3 | |
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| 10. Round | 09/10/1999 | Boca Juniors | - | Instituto de Córdoba | 2:0 | |
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| 11. Round | 16/10/1999 | River Plate | - | Boca Juniors | 2:0 | ||||
| 12. Round | 29/10/1999 | Rosario Central | - | Boca Juniors | 1:3 | |
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| 13. Round | 06/11/1999 | Boca Juniors | - | Newell's Old Boys | 2:1 | ||||
| 14. Round | 12/11/1999 | Colón de Santa Fe | - | Boca Juniors | 1:2 | |
Argentina
Italy