| 3. Jornada | 06.07.2008 | Provincial Osorno (old) | - | Ñublense | 4:1 | ||||
| 8. Jornada | 10.08.2008 | Provincial Osorno (old) | - | Antofagasta | 0:1 |  |
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| 9. Jornada | 17.08.2008 | Provincial Osorno (old) | - | Cobresal | 0:3 | |
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| 10. Jornada | 23.08.2008 | Audax Italiano | - | Provincial Osorno (old) | 1:2 | ||||
| 11. Jornada | 31.08.2008 | Provincial Osorno (old) | - | Universidad de Chile | 1:2 | ||||
| 13. Jornada | 20.09.2008 | Provincial Osorno (old) | - | O'Higgins | 1:1 | |
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| 14. Jornada | 28.09.2008 | Cobreloa | - | Provincial Osorno (old) | 4:0 | ||||
| 15. Jornada | 06.10.2008 | Provincial Osorno (old) | - | La Serena | 1:2 |
Chile