| 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 | ||||
| 8. Round | 10/08/2008 | Provincial Osorno (old) | - | Antofagasta | 0:1 |  |
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| 13. Round | 20/09/2008 | Provincial Osorno (old) | - | O'Higgins | 1:1 | ||||
| 15. Round | 05/10/2008 | Provincial Osorno (old) | - | La Serena | 1:2 | ||||
| 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 | |
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| 19. Round | 09/11/2008 | Provincial Osorno (old) | - | Unión Española | 1:2 |
Chile