| 1. Ronde | 22.06.2008 | Santiago Morning | - | Universidad Católica | 1:0 | ||||
| 3. Ronde | 06.07.2008 | Huachipato | - | Santiago Morning | 1:1 |  |
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| 4. Ronde | 12.07.2008 | Palestino | - | Santiago Morning | 1:1 | ||||
| 5. Ronde | 20.07.2008 | Santiago Morning | - | Antofagasta | 2:1 | |
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| 6. Ronde | 27.07.2008 | O'Higgins | - | Santiago Morning | 4:1 | ||||
| 7. Ronde | 03.08.2008 | Santiago Morning | - | Unión Española | 1:2 | ||||
| 10. Ronde | 24.08.2008 | Santiago Morning | - | Rangers | 1:1 | |
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| 12. Ronde | 14.09.2008 | Everton | - | Santiago Morning | 0:1 | ||||
| 13. Ronde | 20.09.2008 | Santiago Morning | - | Universidad de Chile | 0:3 | ||||
| 14. Ronde | 28.09.2008 | Cobresal | - | Santiago Morning | 4:1 | ||||
| 15. Ronde | 05.10.2008 | Santiago Morning | - | Cobreloa | 3:1 | |
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| 16. Ronde | 19.10.2008 | Provincial Osorno (old) | - | Santiago Morning | 0:1 | ||||
| 17. Ronde | 25.10.2008 | Santiago Morning | - | Audax Italiano | 3:5 | ||||
| 18. Ronde | 01.11.2008 | Deportes Melipilla | - | Santiago Morning | 1:5 | ||||
| 19. Ronde | 09.11.2008 | Santiago Morning | - | La Serena | 3:2 |
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