1. Round | 01/02/2009 | Santiago Morning | - | Cobreloa | 2:0 | ||||
2. Round | 07/02/2009 | Audax Italiano | - | Santiago Morning | 1:1 | ||||
3. Round | 14/02/2009 | Ñublense | - | Santiago Morning | 2:1 | ||||
10. Round | 05/04/2009 | Everton | - | Santiago Morning | 1:3 | ||||
16. Round | 09/05/2009 | Santiago Morning | - | Rangers | 2:1 |