| 2. Ronde | 29.06.2008 | Provincial Osorno (old) | - | Huachipato | 3:1 | ||||
| 3. Ronde | 06.07.2008 | Provincial Osorno (old) | - | Ñublense | 4:1 | ||||
| 4. Ronde | 13.07.2008 | Rangers | - | Provincial Osorno (old) | 1:0 | ||||
| 1. Ronde | 16.07.2008 | Colo-Colo | - | Provincial Osorno (old) | 4:1 |  |
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| 5. Ronde | 21.07.2008 | Provincial Osorno (old) | - | Universidad Católica | 2:4 | |
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| 6. Ronde | 26.07.2008 | Universidad de Concepción | - | Provincial Osorno (old) | 4:1 | |
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| 7. Ronde | 03.08.2008 | Deportes Melipilla | - | Provincial Osorno (old) | 3:1 | |
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| 8. Ronde | 10.08.2008 | Provincial Osorno (old) | - | Antofagasta | 0:1 | |
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| 10. Ronde | 23.08.2008 | Audax Italiano | - | Provincial Osorno (old) | 1:2 | ||||
| 14. Ronde | 28.09.2008 | Cobreloa | - | Provincial Osorno (old) | 4:0 | ||||
| 15. Ronde | 06.10.2008 | Provincial Osorno (old) | - | La Serena | 1:2 | |
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| 16. Ronde | 19.10.2008 | Provincial Osorno (old) | - | Santiago Morning | 0:1 | ||||
| 17. Ronde | 25.10.2008 | Palestino | - | Provincial Osorno (old) | 1:0 |
Chili