| 1. Round | 01/02/2009 | Rangers | - | La Serena | 1:1 | ||||
| 8. Round | 23/04/2009 | La Serena | - | Everton | 1:3 | ||||
| 14. Round | 26/04/2009 | La Serena | - | Santiago Morning | 1:4 | ||||
| 15. Round | 02/05/2009 | Universidad de Chile | - | La Serena | 3:2 | ||||
| 16. Round | 10/05/2009 | La Serena | - | O'Higgins | 1:2 |  |
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| 17. Round | 17/05/2009 | Municipal Iquique | - | La Serena | 2:0 |  |
Chile