| 1. Round | 10/07/2008 | Everton | - | Cobresal | 2:0 | ||||
| 6. Round | 26/07/2008 | Everton | - | La Serena | 5:5 | ||||
| 7. Round | 02/08/2008 | Audax Italiano | - | Everton | 2:1 |  |
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| 8. Round | 10/08/2008 | Everton | - | Deportes Melipilla | 2:1 | ||||
| 9. Round | 17/08/2008 | Rangers | - | Everton | 2:0 | ||||
| 10. Round | 24/08/2008 | Everton | - | Unión Española | 2:0 | ||||
| 11. Round | 31/08/2008 | Huachipato | - | Everton | 2:1 | ||||
| 12. Round | 14/09/2008 | Everton | - | Santiago Morning | 0:1 | ||||
| 13. Round | 21/09/2008 | Ñublense | - | Everton | 1:0 | ||||
| 17. Round | 25/10/2008 | Cobreloa | - | Everton | 2:0 |
Chile