| 2. Round | 03/02/2008 | Huachipato | - | Provincial Osorno (old) | 0:2 | ||||
| 6. Round | 23/02/2008 | Provincial Osorno (old) | - | Universidad de Concepción | 1:3 | ||||
| 7. Round | 01/03/2008 | Provincial Osorno (old) | - | Deportes Melipilla | 3:1 |  |
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| 8. Round | 05/03/2008 | Antofagasta | - | Provincial Osorno (old) | 1:1 | ||||
| 9. Round | 09/03/2008 | Cobresal | - | Provincial Osorno (old) | 2:0 | ||||
| 10. Round | 12/03/2008 | Provincial Osorno (old) | - | Audax Italiano | 1:3 | ||||
| 11. Round | 16/03/2008 | Universidad de Chile | - | Provincial Osorno (old) | 4:1 | ||||
| 12. Round | 23/03/2008 | Provincial Osorno (old) | - | Deportes Concepción | 1:3 | |
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| 13. Round | 29/03/2008 | O'Higgins | - | Provincial Osorno (old) | 4:1 | ||||
| 14. Round | 06/04/2008 | Provincial Osorno (old) | - | Cobreloa | 1:2 | ||||
| 15. Round | 13/04/2008 | La Serena | - | Provincial Osorno (old) | 2:1 | ||||
| 16. Round | 20/04/2008 | Santiago Morning | - | Provincial Osorno (old) | 2:1 | ||||
| 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 |
Argentina
Spain