| 2. Round | 29/06/2008 | Provincial Osorno (old) | - | Huachipato | 3:1 | ||||
| 9. Round | 17/08/2008 | Provincial Osorno (old) | - | Cobresal | 0:3 | ||||
| 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 |  |
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| 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