| 2. Jornada | 29.06.2008 | Provincial Osorno (old) | - | Huachipato | 3:1 | ||||
| 3. Jornada | 06.07.2008 | Provincial Osorno (old) | - | Ñublense | 4:1 | ||||
| 4. Jornada | 13.07.2008 | Rangers | - | Provincial Osorno (old) | 1:0 | ||||
| 1. Jornada | 16.07.2008 | Colo-Colo | - | Provincial Osorno (old) | 4:1 | ||||
| 5. Jornada | 21.07.2008 | Provincial Osorno (old) | - | Universidad Católica | 2:4 | ||||
| 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 |  |
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| 13. Jornada | 20.09.2008 | Provincial Osorno (old) | - | O'Higgins | 1:1 | ||||
| 14. Jornada | 28.09.2008 | Cobreloa | - | Provincial Osorno (old) | 4:0 | ||||
| 17. Jornada | 25.10.2008 | Palestino | - | Provincial Osorno (old) | 1:0 | ||||
| 18. Jornada | 01.11.2008 | Everton | - | Provincial Osorno (old) | 3:1 |
Chile