| 4. Jornada | 13.07.2008 | Audax Italiano | - | Deportes Melipilla | 2:2 | ||||
| 5. Jornada | 20.07.2008 | Deportes Melipilla | - | Ñublense | 1:1 | ||||
| 6. Jornada | 27.07.2008 | Universidad de Chile | - | Deportes Melipilla | 4:1 | ||||
| 7. Jornada | 03.08.2008 | Deportes Melipilla | - | Provincial Osorno (old) | 3:1 | ||||
| 9. Jornada | 21.08.2008 | Deportes Melipilla | - | O'Higgins | 2:1 | ||||
| 12. Jornada | 14.09.2008 | Cobreloa | - | Deportes Melipilla | 2:0 | ||||
| 14. Jornada | 28.09.2008 | Deportes Melipilla | - | Rangers | 0:1 | ||||
| 15. Jornada | 04.10.2008 | Huachipato | - | Deportes Melipilla | 2:1 | ||||
| 17. Jornada | 25.10.2008 | Antofagasta | - | Deportes Melipilla | 4:2 | ||||
| 19. Jornada | 08.11.2008 | Universidad de Concepción | - | Deportes Melipilla | 0:1 |  |
Chile