| 4. Jornada | 12.07.2008 | Palestino | - | Santiago Morning | 1:1 | ||||
| 5. Jornada | 20.07.2008 | Santiago Morning | - | Antofagasta | 2:1 | ||||
| 6. Jornada | 27.07.2008 | O'Higgins | - | Santiago Morning | 4:1 | ||||
| 9. Jornada | 17.08.2008 | Santiago Morning | - | Ñublense | 2:2 | ||||
| 10. Jornada | 24.08.2008 | Santiago Morning | - | Rangers | 1:1 |  |
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| 11. Jornada | 31.08.2008 | Colo-Colo | - | Santiago Morning | 2:1 | ||||
| 12. Jornada | 14.09.2008 | Everton | - | Santiago Morning | 0:1 | ||||
| 13. Jornada | 20.09.2008 | Santiago Morning | - | Universidad de Chile | 0:3 | ||||
| 14. Jornada | 28.09.2008 | Cobresal | - | Santiago Morning | 4:1 | ||||
| 15. Jornada | 05.10.2008 | Santiago Morning | - | Cobreloa | 3:1 | |
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| 16. Jornada | 19.10.2008 | Provincial Osorno (old) | - | Santiago Morning | 0:1 | ||||
| 17. Jornada | 25.10.2008 | Santiago Morning | - | Audax Italiano | 3:5 | ||||
| 18. Jornada | 01.11.2008 | Deportes Melipilla | - | Santiago Morning | 1:5 | ||||
| 19. Jornada | 09.11.2008 | Santiago Morning | - | La Serena | 3:2 | |
Chile