| 1. Round | 21/06/2008 | Unión Española | - | Deportes Melipilla | 1:0 | ||||
| 2. Round | 29/06/2008 | Deportes Melipilla | - | Colo-Colo | 0:2 | ||||
| 3. Round | 06/07/2008 | La Serena | - | Deportes Melipilla | 1:0 | ||||
| 5. Round | 20/07/2008 | Deportes Melipilla | - | Ñublense | 1:1 | ||||
| 7. Round | 03/08/2008 | Deportes Melipilla | - | Provincial Osorno (old) | 3:1 |  |
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| 8. Round | 10/08/2008 | Everton | - | Deportes Melipilla | 2:1 | ||||
| 9. Round | 21/08/2008 | Deportes Melipilla | - | O'Higgins | 2:1 | |
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| 11. Round | 31/08/2008 | Deportes Melipilla | - | Cobresal | 1:2 | ||||
| 12. Round | 14/09/2008 | Cobreloa | - | Deportes Melipilla | 2:0 | ||||
| 13. Round | 21/09/2008 | Deportes Melipilla | - | Universidad Católica | 3:5 | |
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| 14. Round | 28/09/2008 | Deportes Melipilla | - | Rangers | 0:1 | ||||
| 15. Round | 04/10/2008 | Huachipato | - | Deportes Melipilla | 2:1 | |
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| 16. Round | 19/10/2008 | Deportes Melipilla | - | Palestino | 0:2 |  |
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| 18. Round | 31/10/2008 | Deportes Melipilla | - | Santiago Morning | 1:5 | ||||
| 19. Round | 08/11/2008 | Universidad de Concepción | - | Deportes Melipilla | 0:1 |
Chile