| 1. Round | 12/07/2009 | Universidad Católica | - | Municipal Iquique | 2:0 | ||||
| 3. Round | 26/07/2009 | Municipal Iquique | - | Everton | 1:2 | ||||
| 4. Round | 01/08/2009 | Palestino | - | Municipal Iquique | 1:1 | ||||
| 5. Round | 09/08/2009 | Municipal Iquique | - | Unión Española | 3:4 |  |
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| 6. Round | 16/08/2009 | Municipal Iquique | - | Universidad de Chile | 0:2 | ||||
| 7. Round | 23/08/2009 | Santiago Morning | - | Municipal Iquique | 3:2 | ||||
| 8. Round | 30/08/2009 | Municipal Iquique | - | Ñublense | 1:3 | |
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| 9. Round | 13/09/2009 | Audax Italiano | - | Municipal Iquique | 2:0 | ||||
| 10. Round | 20/09/2009 | Municipal Iquique | - | Colo-Colo | 1:1 | ||||
| 11. Round | 23/09/2009 | Universidad de Concepción | - | Municipal Iquique | 2:0 |  |
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| 12. Round | 27/09/2009 | Rangers | - | Municipal Iquique | 5:3 | ||||
| 13. Round | 03/10/2009 | Municipal Iquique | - | Huachipato | 2:2 | |
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| 14. Round | 18/10/2009 | O'Higgins | - | Municipal Iquique | 2:2 | ||||
| 15. Round | 25/10/2009 | Municipal Iquique | - | Cobresal | 1:1 | ||||
| 16. Round | 01/11/2009 | Municipal Iquique | - | Cobreloa | 2:1 | ||||
| 17. Round | 08/11/2009 | La Serena | - | Municipal Iquique | 2:1 | |
Paraguay