| 3. Round | 06/07/2008 | Provincial Osorno (old) | - | Ñublense | 4:1 | ||||
| 8. Round | 10/08/2008 | Provincial Osorno (old) | - | Antofagasta | 0:1 |  |
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| 9. Round | 17/08/2008 | Provincial Osorno (old) | - | Cobresal | 0:3 | |
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| 10. Round | 23/08/2008 | Audax Italiano | - | Provincial Osorno (old) | 1:2 | ||||
| 11. Round | 31/08/2008 | Provincial Osorno (old) | - | Universidad de Chile | 1:2 | ||||
| 13. Round | 20/09/2008 | Provincial Osorno (old) | - | O'Higgins | 1:1 | |
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| 14. Round | 28/09/2008 | Cobreloa | - | Provincial Osorno (old) | 4:0 | ||||
| 15. Round | 05/10/2008 | Provincial Osorno (old) | - | La Serena | 1:2 |
Chile