| 1. Round | 01/02/2009 | Municipal Iquique | - | Universidad Católica | 0:4 |  |
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| 3. Round | 13/02/2009 | Everton | - | Municipal Iquique | 1:0 | ||||
| 4. Round | 22/02/2009 | Municipal Iquique | - | Palestino | 3:0 | ||||
| 5. Round | 25/02/2009 | Unión Española | - | Municipal Iquique | 2:0 | ||||
| 6. Round | 28/02/2009 | Universidad de Chile | - | Municipal Iquique | 0:0 | |
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| 7. Round | 08/03/2009 | Municipal Iquique | - | Santiago Morning | 2:2 | |
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| 11. Round | 29/03/2009 | Municipal Iquique | - | Universidad de Concepción | 1:1 |  |
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| 10. Round | 04/04/2009 | Colo-Colo | - | Municipal Iquique | 1:2 | ||||
| 12. Round | 12/04/2009 | Municipal Iquique | - | Rangers | 1:1 | ||||
| 13. Round | 18/04/2009 | Huachipato | - | Municipal Iquique | 3:1 | ||||
| 14. Round | 26/04/2009 | Municipal Iquique | - | O'Higgins | 3:1 | ||||
| 15. Round | 02/05/2009 | Cobresal | - | Municipal Iquique | 2:5 | ||||
| 16. Round | 10/05/2009 | Cobreloa | - | Municipal Iquique | 0:2 | ||||
| 17. Round | 17/05/2009 | Municipal Iquique | - | La Serena | 2:0 |
Chile