| 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 | |
|||
| 8. Jornada | 10.08.2008 | Provincial Osorno (old) | - | Antofagasta | 0:1 | ||||
| 9. Jornada | 17.08.2008 | Provincial Osorno (old) | - | Cobresal | 0:3 | ||||
| 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 | |
|||
| 14. Jornada | 28.09.2008 | Cobreloa | - | Provincial Osorno (old) | 4:0 | ||||
| 15. Jornada | 06.10.2008 | Provincial Osorno (old) | - | La Serena | 1:2 | |
|||
| 16. Jornada | 19.10.2008 | Provincial Osorno (old) | - | Santiago Morning | 0:1 | ||||
| 18. Jornada | 01.11.2008 | Everton | - | Provincial Osorno (old) | 3:1 | ||||
| 19. Jornada | 09.11.2008 | Provincial Osorno (old) | - | Unión Española | 1:2 |
Chile