| 1. Round | 31/01/2009 | Everton | - | Unión Española | 0:1 | ||||
| 2. Round | 07/02/2009 | Universidad de Concepción | - | Everton | 0:0 | ||||
| 3. Round | 13/02/2009 | Everton | - | Municipal Iquique | 1:0 |  |
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| 4. Round | 21/02/2009 | Everton | - | Rangers | 3:2 | |
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| 6. Round | 01/03/2009 | O'Higgins | - | Everton | 0:1 | ||||
| 7. Round | 07/03/2009 | Everton | - | Universidad de Chile | 1:1 | ||||
| 5. Round | 29/03/2009 | Ñublense | - | Everton | 1:1 | ||||
| 10. Round | 05/04/2009 | Everton | - | Santiago Morning | 1:3 |  |
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| 12. Round | 10/04/2009 | Everton | - | Huachipato | 5:1 | |
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| 8. Round | 23/04/2009 | La Serena | - | Everton | 1:3 | ||||
| 15. Round | 03/05/2009 | Everton | - | Palestino | 1:1 | |
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| 14. Round | 07/05/2009 | Everton | - | Cobresal | 1:1 | |
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| 16. Round | 10/05/2009 | Audax Italiano | - | Everton | 0:1 | ||||
| 17. Round | 17/05/2009 | Everton | - | Curicó Unido | 3:2 |
Chile