| 4. Journée | 12.07.2008 | Palestino | - | Santiago Morning | 1:1 | ||||
| 6. Journée | 27.07.2008 | O'Higgins | - | Santiago Morning | 4:1 | ||||
| 7. Journée | 03.08.2008 | Santiago Morning | - | Unión Española | 1:2 | ||||
| 8. Journée | 09.08.2008 | Universidad de Concepción | - | Santiago Morning | 2:2 |  |
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| 9. Journée | 17.08.2008 | Santiago Morning | - | Ñublense | 2:2 | |
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| 10. Journée | 24.08.2008 | Santiago Morning | - | Rangers | 1:1 | ||||
| 11. Journée | 31.08.2008 | Colo-Colo | - | Santiago Morning | 2:1 | |
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| 14. Journée | 28.09.2008 | Cobresal | - | Santiago Morning | 4:1 |  |
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| 16. Journée | 19.10.2008 | Provincial Osorno (old) | - | Santiago Morning | 0:1 | |
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| 18. Journée | 01.11.2008 | Deportes Melipilla | - | Santiago Morning | 1:5 | ||||
| 19. Journée | 09.11.2008 | Santiago Morning | - | La Serena | 3:2 | |
Chili