| 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 | ||||
| 6. Round | 26/07/2008 | Universidad de Concepción | - | Provincial Osorno (old) | 4:1 | ||||
| 7. Round | 03/08/2008 | Deportes Melipilla | - | Provincial Osorno (old) | 3:1 |  |
Argentina
Spain