| 2. Round | 29/06/2008 | Provincial Osorno (old) | - | Huachipato | 3:1 | ||||
| 3. Round | 06/07/2008 | Provincial Osorno (old) | - | Ñublense | 4:1 | ||||
| 4. Round | 13/07/2008 | Rangers | - | Provincial Osorno (old) | 1:0 | ||||
| 1. Round | 16/07/2008 | Colo-Colo | - | Provincial Osorno (old) | 4:1 | ||||
| 5. Round | 20/07/2008 | Provincial Osorno (old) | - | Universidad Católica | 2:4 | ||||
| 9. Round | 17/08/2008 | Provincial Osorno (old) | - | Cobresal | 0:3 |  |
Chile