Second Round
| September 25, 2008 | |||
| Fernández Vial | 2-4 | Colo-Colo | |
| October 1, 2008 | |||
| Unión La Calera | 1-1 | Everton | |
| October 2, 2008 | |||
| Deportes Tocopilla | 1-3 | Cobreloa | |
| Deportivo Ormazábal | 0-1 | Deportes Antofagasta | |
| Santiago Wanderers | 1-0 | Universidad de Chile | |
| October 7, 2008 | |||
| Magallanes | 0-2 | Cobresal | |
| October 8, 2008 | |||
| Lota Schwager | 0-0 | Universidad de Concepción | |
| San Luis | 0-2 | Unión Española | |
| Deportes Ovalle | 0-0 | Deportes La Serena | |
| Provincial Talagante | 0-1 | Deportes Melipilla | |
| Deportes Valdivia | 0-6 | Provincial Osorno | |
| Unión San Felipe | 2-2 | Rangers | |
| Curicó Unido | 1-2 | O'Higgins | |
| October 9, 2008 | |||
| Audax Italiano | 3-0 | Universidad Católica | |
| October 11, 2008 | |||
| Palestino | 0-1 | Santiago Morning | |
| Ñublense | 1-1 | Huachipato |
Read more about this topic: 2008 Copa Chile
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