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 | ||||
6. Round | 01/03/2009 | Santiago Morning | - | Universidad de Concepción | 5:4 | ||||
11. Round | 28/03/2009 | Santiago Morning | - | Curicó Unido | 0:1 | ||||
10. Round | 05/04/2009 | Everton | - | Santiago Morning | 1:3 | ||||
12. Round | 11/04/2009 | Universidad de Chile | - | Santiago Morning | 1:3 | ||||
13. Round | 19/04/2009 | Santiago Morning | - | Unión Española | 1:3 | ||||
14. Round | 26/04/2009 | La Serena | - | Santiago Morning | 1:4 | ||||
16. Round | 09/05/2009 | Santiago Morning | - | Rangers | 2:1 | ||||
17. Round | 16/05/2009 | O'Higgins | - | Santiago Morning | 3:2 |