First Round
| August 13, 2008 | ||||
| Unión Temuco | 2-4 | Fernández Vial | ||
| Malleco Unido | 1-1 | Lota Schwager | ||
| August 26, 2008 | ||||
| Deportivo Ormazábal | 2-1 | San Marcos de Arica | ||
| August 27, 2008 | ||||
| Unión Quilpué | 0-2 | San Luis | ||
| Provincial Talagante | 1-1 | Unión San Felipe* | ||
| Linares Unido | 1-1 | Curicó Unido | ||
| Deportes Tocopilla | 1-1 | Municipal Iquique | ||
| September 11, 2008 | ||||
| Deportes Ovalle | 3-1 | Coquimbo Unido | ||
| Deportes Santa Cruz | 1-3 | Unión La Calera | ||
| September 14, 2008 | ||||
| Deportes Valdivia | 1-0 | Deportes Puerto Montt | ||
| September 17, 2008 | ||||
| Magallanes | 1-0 | Deportes Copiapó | ||
| September 18, 2008 | ||||
| Selección Coyhaique | 0-6 | Santiago Wanderers |
Read more about this topic: 2008 Copa Chile
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