| 1. Round | 01/02/2009 | Santiago Morning | - | Cobreloa | 2:0 |  |
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| 2. Round | 07/02/2009 | Audax Italiano | - | Santiago Morning | 1:1 | |
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| 3. Round | 14/02/2009 | Ñublense | - | Santiago Morning | 2:1 | |
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| 4. Round | 21/02/2009 | Santiago Morning | - | Huachipato | 5:0 | ||||
| 5. Round | 26/02/2009 | Colo-Colo | - | Santiago Morning | 4:2 | |
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| 7. Round | 08/03/2009 | Municipal Iquique | - | Santiago Morning | 2:2 | ||||
| 8. Round | 15/03/2009 | Santiago Morning | - | Cobresal | 3:3 | ||||
| 11. Round | 28/03/2009 | Santiago Morning | - | Curicó Unido | 0:1 | |
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| 13. Round | 19/04/2009 | Santiago Morning | - | Unión Española | 1:3 | ||||
| 15. Round | 03/05/2009 | Santiago Morning | - | Universidad Católica | 0:1 | ||||
| 16. Round | 09/05/2009 | Santiago Morning | - | Rangers | 2:1 | ||||
| 17. Round | 16/05/2009 | O'Higgins | - | Santiago Morning | 3:2 |
Chile