| 6. Round | 26/07/2008 | Universidad de Concepción | - | Provincial Osorno (old) | 4:1 | ||||
| 13. Round | 20/09/2008 | Provincial Osorno (old) | - | O'Higgins | 1:1 | ||||
| 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 | ||||
| 19. Round | 09/11/2008 | Provincial Osorno (old) | - | Unión Española | 1:2 |
Chile