The 2008 Copa Chile 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.
| Round | Date |
|---|---|
| Preliminary Round | 6–27 July 2008 |
| First Round | 13 August 18 September 2008 |
| Second Round | 25 September 11 October 2008 |
| Third Round | 16–30 October 2008 |
| Quarterfinals | 3–5 February 2009 |
| Semifinals | 11 February 2009 |
| Final | 17 February 2009 |
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Selección Punta Arenas | 2–7 | Magallanes | 1–2 | 1–5 |
| Deportivo Lo Barnechea | 4–6 | Provincial Talagante | 1–3 | 3–3 |
| Deportes Tocopilla | 3–3 (5-4p) | Municipal Mejillones | 2–1 | 1–2 |
| Unión Temuco | 5–2 | Deportes Temuco | 3–0 | 2–2 |
| Naval | 0–2 | Deportes Valdivia | 0–2 | 0–0 |
| Unión Bellavista | 6–10 | Deportivo Ormazábal | 4–4 | 2–6 |
| Ferroviarios | 3–3 (a) | Deportes Ovalle | 3–3 | 0–0 |
| Trasandino | 0–3 | Linares Unido | 0–1 | 0–2 |
| Malleco Unido | 3–1 | Iberia | 1–1 | 2–0 |
| Cabildo AGC | 4–5 | Unión Quilpué | 1–2 | 3–3 |
| Deportes Santa Cruz | 4–4 (a) | Deportes Colchagua | 3–0 | 1–4 |
| Selección Coyhaique | 6–5 | Selección Puerto Aysén | 4–1 | 2–4 |
| Home team | Score | Away team |
|---|---|---|
| Unión Temuco | 2–4 | Fernández Vial |
| Malleco Unido | 1–1 (2-4p) | Lota Schwager |
| Deportivo Ormazábal | 2–1 | San Marcos de Arica |
| Unión Quilpué | 0–2 | San Luis |
| Provincial Talagante | 1–1 (6-5p) | Unión San Felipe* |
| Linares Unido | 1–1 (5-6p) | Curicó Unido |
| Deportes Tocopilla | 1–1 (7-6p) | 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"
| Home team | Score | Away team |
|---|---|---|
| Fernández Vial | 2–4 | Colo-Colo |
| Unión La Calera | 1–1 (4-3p) | Everton |
| Deportes Tocopilla | 1–3 | Cobreloa |
| Deportivo Ormazábal | 0–1 | Deportes Antofagasta |
| Santiago Wanderers | 1–0 | Universidad de Chile |
| Magallanes | 0–2 | Cobresal |
| Lota Schwager | 0–0 (3-4p) | Universidad de Concepción |
| San Luis | 0–2 | Unión Española |
| Deportes Ovalle | 0–0 (5-4p) | Deportes La Serena |
| Provincial Talagante | 0–1 | Deportes Melipilla |
| Deportes Valdivia | 0–6 | Provincial Osorno |
| Unión San Felipe | 2–2 (4-5p) | Rangers |
| Curicó Unido | 1–2 | O'Higgins |
| Audax Italiano | 3–0 | Universidad Católica |
| Palestino | 0–1 | Santiago Morning |
| Ñublense | 1–1 (3-5p) | Huachipato |
| Home team | Score | Away team |
|---|---|---|
| Unión Española | 4–3 | Santiago Morning |
| Santiago Wanderers | 2–2 (4-3p) | Audax Italiano |
| Huachipato | 2–1 | O'Higgins |
| Deportes Melipilla | 2–1 | Rangers |
| Cobreloa | 0–0 (5-4p) | Deportes Antofagasta |
| Provincial Osorno | 1–1 (1-4p) | Universidad de Concepción |
| Deportes Ovalle | 1–1 (4-3p) | Cobresal |
| Union La Calera | 3–3 (4-5p) | Colo-Colo |
| Home team | Score | Away team |
|---|---|---|
| Cobreloa | 0–3 | Universidad de Concepción |
| Deportes Ovalle | 2–2 (4-1p) | Colo-Colo |
| Santiago Wanderers | 0–0 (2-4p) | Huachipato |
| Deportes Melipilla | 0–1 | Unión Española |
| Deportes Ovalle | 2 – 2 | Huachipato |
|---|---|---|
Canales  40' Canales 52' |
Llanos 58' García 87' |
|
| Penalties | ||
Sanchez  Saez Cadiz |
3–0 |  Currimilla Zelaye García |
| Unión Española | 1 – 2 | Universidad de Concepción |
|---|---|---|
| Sierra 3' |
Laffatigue 10' Vargas 13' |
| Deportes Ovalle | 1 – 2 | Universidad de Concepción |
|---|---|---|
| G. Soto 5' |
Vargas 10' Solís 51' |
| Copa Chile 2008 Champion |
|---|
 U. de Concepción First Title |
| Goalscorers | Goals | Team |
|---|---|---|
 Lucas Barrios
|
4
|
Colo-Colo |
 Gamadiel García
|
4
|
Huachipato |
| Manuel Neira
|
4
|
Unión Española |
| Carlos Espinosa
|
3
|
Deportes Melipilla |
| Joel Soto
|
3
|
Santiago Wanderers |
| Esteban Paredes
|
3
|
Santiago Morning |
| Julio César Laffatigue
|
3
|
Universidad de Concepción |
