Quarterfinals
| February 3, 2009 | |||
| Cobreloa | 0-3 | Universidad de Concepción | |
| Deportes Ovalle | 2-2 | Colo-Colo | |
| February 5, 2009 | |||
| Santiago Wanderers | 0-0 | Huachipato | |
| Deportes Melipilla | 0-1 | Unión Española |
Read more about this topic: 2008 Copa Chile
Quarterfinals
| February 3, 2009 | |||
| Cobreloa | 0-3 | Universidad de Concepción | |
| Deportes Ovalle | 2-2 | Colo-Colo | |
| February 5, 2009 | |||
| Santiago Wanderers | 0-0 | Huachipato | |
| Deportes Melipilla | 0-1 | Unión Española |
Read more about this topic: 2008 Copa Chile