Copa Chile 2008/2009 var 2008/09 års säsong av Copa Chile och den första säsongen av turneringen sedan 2000 och den 29:e turneringen totalt. Universidad de Concepción stod som vinnare efter en finalseger mot Deportes Ovalle.
| Lag | Resultat | Lag | Match 1 | Match 2 | Bortamål | Straffar |
|---|---|---|---|---|---|---|
| Unión Bellavista | 6 – 10 | Revisora Ormazábal | 4 – 4 | 2 – 6 | — | — |
| Deportes Tocopilla (s) | 3 – 3 | Municipal Mejillones | 2 – 1 | 1 – 2 | 1 – 1 | 5 – 4 |
| Ferroviarios | 3 – 3 | Deportes Ovalle (b) | 3 – 3 | 0 – 0 | 0 – 3 | — |
| Cabildo AGC | 4 – 5 | Unión Quilpué | 1 – 2 | 3 – 3 | — | — |
| Barnechea | 4 – 6 | Provincial Talagante | 1 – 3 | 3 – 3 | — | — |
| Trasandino | 0 – 3 | Linares Unido | 0 – 1 | 0 – 2 | — | — |
| Santa Cruz (b) | 4 – 4 | Colchagua | 3 – 0 | 1 – 4 | 1 – 0 | — |
| Naval | 0 – 2 | Deportes Valdivia | 0 – 2 | 0 – 0 | — | — |
| Malleco Unido | 3 – 1 | Iberia | 1 – 1 | 2 – 0 | — | — |
| Unión Temuco | 5 – 2 | Deportes Temuco | 3 – 0 | 2 – 2 | — | — |
| San Juan | 6 – 5 | Puerto Ayséns stadslag | 4 – 1 | 2 – 4 | — | — |
| Punta Arenas stadslag | 2 – 7 | Magallanes | 1 – 2 | 1 – 5 | — | — |
| Lag | Resultat | Lag | Straffar |
|---|---|---|---|
| Revisora Ormazábal | 6 – 10 | San Marcos de Arica | — |
| Deportes Tocopilla (s) | 1 – 1 | Municipal Iquique | 7 – 6 |
| Deportes Ovalle | 3 – 1 | Coquimbo Unido | — |
| Unión Quilpué | 0 – 2 | San Luis | — |
| Provincial Talagante (s) | 1 – 1 | Unión San Felipe (bästa förlorare) | 6 – 5 |
| Linares Unido | 1 – 1 | Curicó Unido (s) | 5 – 6 |
| Deportes Santa Cruz | 1 – 3 | Unión La Calera | — |
| Deportes Valdivia | 1 – 0 | Deportes Puerto Montt | — |
| Malleco Unido | 1 – 1 | Lota Schwager (s) | 2 – 4 |
| Unión Temuco | 2 – 4 | Fernández Vial | — |
| San Juan | 0 – 6 | Santiago Wanderers | — |
| Magallanes | 1 – 0 | Deportes Copiapó | — |
| Lag | Resultat | Lag | Straffar |
|---|---|---|---|
| Revisora Ormazábal | 0 – 1 | Deportes Antofagasta | — |
| Deportes Tocopilla | 1 – 3 | Cobreloa | — |
| Deportes Magallanes | 0 – 2 | Cobresal | — |
| Deportes Ovalle (s) | 0 – 0 | Deportes La Serena | 5 – 4 |
| San Luis | 0 – 2 | Unión Española | — |
| Audax Italiano | 3 – 0 | Universidad Católica | — |
| Provincial Talagante | 1 – 3 | Deportes Melipilla | — |
| Palestino | 0 – 1 | Santiago Morning | — |
| Curicó Unido | 1 – 2 | O'Higgins | — |
| Unión San Felipe | 2 – 2 | Rangers (s) | 4 – 5 |
| Unión La Calera (s) | 1 – 1 | Everton | 4 – 3 |
| Ñublense | 1 – 1 | Huachipato (s) | 3 – 5 |
| Deportes Valdivia | 0 – 6 | Provincial Osorno | — |
| Lota Schwager | 0 – 0 | Universidad de Concepción (s) | 3 – 4 |
| Fernández Vial | 2 – 4 | Colo-Colo | — |
| Santiago Wanderers | 1 – 0 | Universidad de Chile | — |
| Lag | Resultat | Lag | Straffar |
|---|---|---|---|
| Cobreloa (s) | 0 – 0 | Deportes Antofagasta | 5 – 4 |
| Deportes Ovalle (s) | 1 – 1 | Cobresal | 4 – 3 |
| Unión La Calera | 3 – 3 | Colo-Colo (s) | 4 – 5 |
| Santiago Wanderers (s) | 2 – 2 | Audax Italiano | 4 – 3 |
| Unión Española | 4 – 3 | Santiago Morning | — |
| Deportes Melipilla | 2 – 1 | Rangers | — |
| Huachipato | 2 – 1 | O'Higgins | — |
| Provincial Osorno | 1 – 1 | Universidad de Concepción (s) | 1 – 4 |
| Lag | Resultat | Lag | Straffar |
|---|---|---|---|
| Deportes Ovalle (s) | 2 – 2 | Colo-Colo | 4 – 1 |
| Santiago Wanderers | 0 – 0 | Huachipato (s) | 2 – 4 |
| Cobreloa | 0 – 3 | Universidad de Concepción | — |
| Deportes Melipilla | 0 – 1 | Unión Española | — |
| Lag | Resultat | Lag | Straffar |
|---|---|---|---|
| Deportes Ovalle (s) | 2 – 2 | Colo-Colo | 3 – 0 |
| Universidad de Concepción | 2 – 1 | Huachipato | — |
| Lag | Resultat | Lag | Straffar |
|---|---|---|---|
| Deportes Ovalle | 1 – 2 | Universidad de Concepción | — |
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