| 1. Round | 12/07/2009 | Deportes Tolima | - | Deportes Quindío | 1:4 |  |
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| 2. Round | 19/07/2009 | Atlético Huila | - | Deportes Tolima | 1:0 | ||||
| 3. Round | 27/07/2009 | Millonarios | - | Deportes Tolima | 0:2 | ||||
| 5. Round | 09/08/2009 | Atlético Nacional | - | Deportes Tolima | 2:2 | |
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| 6. Round | 16/08/2009 | Deportes Tolima | - | Once Caldas | 2:1 | ||||
| 12. Round | 04/10/2009 | Santa Fe | - | Deportes Tolima | 1:1 | ||||
| 13. Round | 18/10/2009 | Deportes Tolima | - | Envigado FC | 1:0 | ||||
| 14. Round | 22/10/2009 | Independiente Medellín | - | Deportes Tolima | 1:3 |  |
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| 18. Round | 15/11/2009 | Atlético Junior | - | Deportes Tolima | 2:1 |
Colombia