| 1. Round | 21/06/2008 | Unión Española | - | Deportes Melipilla | 1:0 | ||||
| 9. Round | 21/08/2008 | Deportes Melipilla | - | O'Higgins | 2:1 | ||||
| 11. Round | 31/08/2008 | Deportes Melipilla | - | Cobresal | 1:2 | ||||
| 15. Round | 04/10/2008 | Huachipato | - | Deportes Melipilla | 2:1 | ||||
| 17. Round | 25/10/2008 | Antofagasta | - | Deportes Melipilla | 4:2 |
Chile