| 3. Jornada | 06.07.2008 | La Serena | - | Deportes Melipilla | 1:0 | ||||
| 4. Jornada | 13.07.2008 | Audax Italiano | - | Deportes Melipilla | 2:2 |  |
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| 5. Jornada | 20.07.2008 | Deportes Melipilla | - | Ñublense | 1:1 | |
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| 6. Jornada | 27.07.2008 | Universidad de Chile | - | Deportes Melipilla | 4:1 | ||||
| 7. Jornada | 03.08.2008 | Deportes Melipilla | - | Provincial Osorno (old) | 3:1 | ||||
| 8. Jornada | 10.08.2008 | Everton | - | Deportes Melipilla | 2:1 | ||||
| 11. Jornada | 31.08.2008 | Deportes Melipilla | - | Cobresal | 1:2 | ||||
| 12. Jornada | 14.09.2008 | Cobreloa | - | Deportes Melipilla | 2:0 | |
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| 14. Jornada | 28.09.2008 | Deportes Melipilla | - | Rangers | 0:1 | ||||
| 16. Jornada | 19.10.2008 | Deportes Melipilla | - | Palestino | 0:2 | ||||
| 17. Jornada | 25.10.2008 | Antofagasta | - | Deportes Melipilla | 4:2 | |
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| 18. Jornada | 01.11.2008 | Deportes Melipilla | - | Santiago Morning | 1:5 | ||||
| 19. Jornada | 08.11.2008 | Universidad de Concepción | - | Deportes Melipilla | 0:1 | |
Argentina