| 1. Round | 21/06/2008 | Unión Española | - | Deportes Melipilla | 1:0 | ||||
| 2. Round | 29/06/2008 | Deportes Melipilla | - | Colo-Colo | 0:2 | ||||
| 3. Round | 06/07/2008 | La Serena | - | Deportes Melipilla | 1:0 | ||||
| 4. Round | 13/07/2008 | Audax Italiano | - | Deportes Melipilla | 2:2 | ||||
| 13. Round | 21/09/2008 | Deportes Melipilla | - | Universidad Católica | 3:5 |  |
|||
| 14. Round | 28/09/2008 | Deportes Melipilla | - | Rangers | 0:1 | ||||
| 15. Round | 04/10/2008 | Huachipato | - | Deportes Melipilla | 2:1 | ||||
| 16. Round | 19/10/2008 | Deportes Melipilla | - | Palestino | 0:2 |
Chile