| 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 | ||||
| 16. Jornada | 19.10.2008 | Provincial Osorno (old) | - | Santiago Morning | 0:1 | ||||
| 17. Jornada | 25.10.2008 | Palestino | - | Provincial Osorno (old) | 1:0 | ||||
| 18. Jornada | 01.11.2008 | Everton | - | Provincial Osorno (old) | 3:1 |
Chile