| 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 | ||||
| 13. Round | 20/09/2008 | Provincial Osorno (old) | - | O'Higgins | 1:1 | ||||
| 14. Round | 28/09/2008 | Cobreloa | - | Provincial Osorno (old) | 4:0 | ||||
| 16. Round | 19/10/2008 | Provincial Osorno (old) | - | Santiago Morning | 0:1 | ||||
| 17. Round | 25/10/2008 | Palestino | - | Provincial Osorno (old) | 1:0 | ||||
| 18. Round | 01/11/2008 | Everton | - | Provincial Osorno (old) | 3:1 |
Chile