| 6. Journée | 26.07.2008 | Universidad de Concepción | - | Provincial Osorno (old) | 4:1 | ||||
| 7. Journée | 03.08.2008 | Deportes Melipilla | - | Provincial Osorno (old) | 3:1 | ||||
| 8. Journée | 10.08.2008 | Provincial Osorno (old) | - | Antofagasta | 0:1 |  |
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| 13. Journée | 20.09.2008 | Provincial Osorno (old) | - | O'Higgins | 1:1 | ||||
| 15. Journée | 06.10.2008 | Provincial Osorno (old) | - | La Serena | 1:2 | ||||
| 16. Journée | 19.10.2008 | Provincial Osorno (old) | - | Santiago Morning | 0:1 | ||||
| 17. Journée | 25.10.2008 | Palestino | - | Provincial Osorno (old) | 1:0 | ||||
| 18. Journée | 01.11.2008 | Everton | - | Provincial Osorno (old) | 3:1 | |
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| 19. Journée | 09.11.2008 | Provincial Osorno (old) | - | Unión Española | 1:2 |
Chili