Semifinals
| Universidad de Chile | 2 – 3 | Deportes La Serena |
|---|---|---|
Campos  23', 70' | 7' López18' Pérez67' Aravena |
| Colo-Colo | 0 – 4 | Santiago Wanderers |
|---|---|---|
| 9' Bozzalla18', 70' Reynoso80' Tobar |
The 1959 Copa Chile was the second edition of the Chilean Cup tournament. The competition started on November 21, 1959, and concluded on December 22, 1959. Santiago Wanderers won the competition for the first time, beating Deportes La Serena on the final.
Matches were scheduled to be played at the stadium of the team named first on the date specified for each round. From the beginning of the second Round, if scores were level after 90 minutes had been played, an extra time took place.
| Round | Date |
|---|---|
| First round | 21 November 1959 2 December 1959 |
| Second round | 5–6 December 1959 |
| Quarterfinals | 12 December 1959 |
| Semifinals | 19 December 1959 |
| Finals | 22 December 1959 |
| Teams | Scores | Tie-breakers | |||||
|---|---|---|---|---|---|---|---|
| Team #1 | Agg. | Team #2 | 1st leg | 2nd leg | Replay | ||
| Audax Italiano | 8–3 | San Bernardo Central | 6–1 | 2–2 | — | ||
| Magallanes | 1–1 | Fernández Vial | 1–0 | 0–1 | 4—2 | ||
| Colo-Colo | 6–2 | Selección Arica | 6–0 | 0–2 | — | ||
| Universidad de Chile | 2–0 | Ñublense | 0–0 | 2–0 | — | ||
| Universidad Católica | 5–4 | Deportivo San Fernando | 3–2 | 2–2 | — | ||
| Santiago Wanderers | 6–5 | Unión San Felipe | 4–2 | 2–3 | — | ||
| Unión La Calera | 6–5 | San Luis | 2–3 | 4–2 | — | ||
| O'Higgins | 6–3 | Universidad Técnica | 3–2 | 3–1 | — | ||
| Selección Cauquenes | 1–6 | Unión Española | 1–3 | 0–3 | — | ||
| Selección Calama | 0–7 | Deportes La Serena | 0–1 | 0–6 | — | ||
| Trasandino | 4–2 | Ferrobádminton | 2–1 | 2–1 | — | ||
| Thomas Bata | 5–4 | Green Cross | 3–3 | 2–1 | — | ||
| Selección Copiapó | 2–5 | Santiago Morning | 2–4 | 0–1 | — | ||
| Naval | 2–5 | Palestino | 1–1 | 1–4 | — | ||
| Rangers | 5–3 | Selección Pitrufquén | 5–1 | 0–2 | — | ||
| Coquimbo Unido | 2–7 | Everton | 1–2 | 1–5 | — | ||
| Home team | Score | Away team |
|---|---|---|
| O'Higgins | 3–0 | Unión Española |
| Colo-Colo | 4–0 | Everton |
| Deportes La Serena | 6–0 | Thomas Bata |
| Santiago Wanderers | 4–3 | Unión La Calera |
| Rangers | 3–3 (ct) | Magallanes |
| Palestino | 2–2 (ct) | Trasandino |
| Universidad de Chile | 3–1 | Audax Italiano |
| Universidad Católica | 3–1 | Santiago Morning |
| Home team | Score | Away team |
|---|---|---|
| Universidad de Chile | 5–3 | Magallanes |
| Colo-Colo | 2–1 | O'Higgins |
| Santiago Wanderers | 2–1 | Universidad Católica |
| Deportes La Serena | 1–0 | Trasandino |
| Universidad de Chile | 2 – 3 | Deportes La Serena |
|---|---|---|
| Campos 23', 70' | 7' López18' Pérez67' Aravena |
| Colo-Colo | 0 – 4 | Santiago Wanderers |
|---|---|---|
| 9' Bozzalla18', 70' Reynoso80' Tobar |
| Colo-Colo | 0 – 1 | Universidad de Chile |
|---|---|---|
| 75' Ibarra |
| Santiago Wanderers | 5 – 1 | Deportes La Serena |
|---|---|---|
| R. Díaz 35', 41', 55' Reynoso 49', 73' | 28' (pen.) Farías |
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