| 2. Round | 28/06/2008 | Universidad Católica | - | Everton | 0:1 |  |
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| 3. Round | 05/07/2008 | Everton | - | Universidad de Concepción | 2:1 |  |
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| 1. Round | 10/07/2008 | Everton | - | Cobresal | 2:0 | |
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| 4. Round | 13/07/2008 | Universidad de Chile | - | Everton | 1:2 | |
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| 5. Round | 19/07/2008 | Everton | - | Palestino | 0:1 | ||||
| 6. Round | 26/07/2008 | Everton | - | La Serena | 5:5 | |
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| 7. Round | 02/08/2008 | Audax Italiano | - | Everton | 2:1 | ||||
| 11. Round | 31/08/2008 | Huachipato | - | Everton | 2:1 | |
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| 12. Round | 14/09/2008 | Everton | - | Santiago Morning | 0:1 | |
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| 13. Round | 21/09/2008 | Ñublense | - | Everton | 1:0 | ||||
| 14. Round | 28/09/2008 | Everton | - | Colo-Colo | 3:1 | ||||
| 15. Round | 04/10/2008 | O'Higgins | - | Everton | 4:3 | |
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| 17. Round | 25/10/2008 | Cobreloa | - | Everton | 2:0 | ||||
| 18. Round | 01/11/2008 | Everton | - | Provincial Osorno (old) | 3:1 | |
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| 19. Round | 09/11/2008 | Antofagasta | - | Everton | 0:1 | |
Chile