| 1. Round | 06/03/1999 | Gimnasia de Jujuy | - | Argentinos Juniors | 0:2 | ||||
| 2. Round | 12/03/1999 | Gimnasia de Jujuy | - | Boca Juniors | 0:2 | ||||
| 4. Round | 27/03/1999 | Gimnasia de Jujuy | - | Huracán | 2:2 |  |
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| 7. Round | 08/04/1999 | Racing Club | - | Gimnasia de Jujuy | 2:0 | ||||
| 8. Round | 17/04/1999 | Gimnasia de Jujuy | - | Platense | 1:1 | ||||
| 16. Round | 01/06/1999 | Gimnasia de Jujuy | - | Independiente | 3:1 | |
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| 17. Round | 04/06/1999 | Lanús | - | Gimnasia de Jujuy | 1:2 | ||||
| 18. Round | 12/06/1999 | Gimnasia de Jujuy | - | Unión de Santa Fe | 0:2 |
Argentina