2008–09 Copa Chile
The Copa Chile 2008 was the 29th edition of the tournament. It began on July 6, 2008, and ended on February 17, 2009. The winner of Copa Chile 2008 is eligible to play a berth in the Copa Sudamericana 2009. In the final Universidad de Concepción defeated the third division team Deportes Ovalle 2–1, thereby claiming their first title.
Calendar
Preliminary round
First round
| Home team | Score | Away team |
| Unión Temuco | 2–4 | Fernández Vial |
| Malleco Unido | 1–1 | Lota Schwager |
| Deportivo Ormazábal | 2–1 | San Marcos de Arica |
| 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 |
| Deportes Ovalle | 3–1 | Coquimbo Unido |
| Deportes Santa Cruz | 1–3 | Unión La Calera |
| Deportes Valdivia | 1–0 | Deportes Puerto Montt |
| Magallanes | 1–0 | Deportes Copiapó |
| Selección Coyhaique | 0–6 | Santiago Wanderers |
- Qualified as "Best Loser"
Second round
Third round
Quarterfinals
Semifinals
----Final
| Copa Chile 2008 Champion |
U. de Concepción First Title |
Top goalscorers
| Goalscorers | Goals | Team |
 Lucas Barrios | Colo-Colo | |
 Gamadiel García | Huachipato | |
| Manuel Neira | Unión Española | |
| Carlos Espinosa | Deportes Melipilla | |
| Joel Soto | Santiago Wanderers | |
| Esteban Paredes | Santiago Morning | |
| Julio César Laffatigue | Universidad de Concepción |