| 1. Round | 31/01/2009 | Everton | - | Unión Española | 0:1 | ||||
| 5. Round | 25/02/2009 | Unión Española | - | Municipal Iquique | 2:0 | ||||
| 6. Round | 01/03/2009 | Audax Italiano | - | Unión Española | 2:2 | ||||
| 8. Round | 15/03/2009 | Cobreloa | - | Unión Española | 2:1 |  |
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| 10. Round | 05/04/2009 | La Serena | - | Unión Española | 0:3 | ||||
| 17. Round | 16/05/2009 | Unión Española | - | Ñublense | 1:2 |
Chile