| 3. Round | 14/02/2009 | Ñublense | - | Santiago Morning | 2:1 | ||||
| 6. Round | 01/03/2009 | Santiago Morning | - | Universidad de Concepción | 5:4 | ||||
| 10. Round | 05/04/2009 | Everton | - | Santiago Morning | 1:3 |  |
|||
| 14. Round | 26/04/2009 | La Serena | - | Santiago Morning | 1:4 |  |
|||
| 15. Round | 03/05/2009 | Santiago Morning | - | Universidad Católica | 0:1 | ||||
| 16. Round | 09/05/2009 | Santiago Morning | - | Rangers | 2:1 | ||||
| 17. Round | 16/05/2009 | O'Higgins | - | Santiago Morning | 3:2 | |
Chile