| 1. Round | 22/06/2008 | Santiago Morning | - | Universidad Católica | 1:0 | ||||
| 3. Round | 06/07/2008 | Huachipato | - | Santiago Morning | 1:1 | ||||
| 4. Round | 12/07/2008 | Palestino | - | Santiago Morning | 1:1 | ||||
| 5. Round | 20/07/2008 | Santiago Morning | - | Antofagasta | 2:1 |  |
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| 6. Round | 26/07/2008 | O'Higgins | - | Santiago Morning | 4:1 | ||||
| 7. Round | 03/08/2008 | Santiago Morning | - | Unión Española | 1:2 | ||||
| 10. Round | 24/08/2008 | Santiago Morning | - | Rangers | 1:1 | ||||
| 14. Round | 28/09/2008 | Cobresal | - | Santiago Morning | 4:1 | ||||
| 16. Round | 19/10/2008 | Provincial Osorno (old) | - | Santiago Morning | 0:1 | ||||
| 17. Round | 25/10/2008 | Santiago Morning | - | Audax Italiano | 3:5 |
Chile