| 1. Round | 25/01/2008 | Provincial Osorno (old) | - | Colo-Colo | 0:3 |  |
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| 2. Round | 03/02/2008 | Huachipato | - | Provincial Osorno (old) | 0:2 | ||||
| 3. Round | 10/02/2008 | Ñublense | - | Provincial Osorno (old) | 2:0 | ||||
| 4. Round | 13/02/2008 | Provincial Osorno (old) | - | Rangers | 2:1 | ||||
| 5. Round | 16/02/2008 | Universidad Católica | - | Provincial Osorno (old) | 2:0 | ||||
| 6. Round | 23/02/2008 | Provincial Osorno (old) | - | Universidad de Concepción | 1:3 | |
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| 7. Round | 01/03/2008 | Provincial Osorno (old) | - | Deportes Melipilla | 3:1 | ||||
| 8. Round | 05/03/2008 | Antofagasta | - | Provincial Osorno (old) | 1:1 | ||||
| 9. Round | 09/03/2008 | Cobresal | - | Provincial Osorno (old) | 2:0 | ||||
| 17. Round | 26/04/2008 | Provincial Osorno (old) | - | Palestino | 1:0 | ||||
| 18. Round | 01/05/2008 | Provincial Osorno (old) | - | Everton | 2:1 | ||||
| 19. Round | 03/05/2008 | Unión Española | - | Provincial Osorno (old) | 2:0 | |
Chile