The Copa Invierno 1989 was an official Chilean Cup tournament, whose purpose was to maintain clubs in activity during the 1989 Copa América and 1990 FIFA World Cup qualification (CONMEBOL) recess. The competition started on July 15, 1989, and concluded on August 15, 1989. U. Española won the competition, beating Huachipato 2–0 in the final. Played on mid-1989, the tournament was the second official cup competition of the season 1989.
| Round | Date | |
|---|---|---|
| Group Round | 15–29 July 1989 | |
| Quarterfinals | 5 August 1989 | |
| Semi-finals | 12 August 1989 | |
| Final | 15 August 1989 |
| Rank | Team | Points | |
| 1 | Deportes La Serena | 6 | |
|---|---|---|---|
| 2 | Cobreloa | 4 | |
| 3 | Deportes Iquique | 2 | |
| 4 | Cobresal | 0 |
| Rank | Team | Points | |
| 1 | Everton | 5 | |
|---|---|---|---|
| 2 | Unión Española | 4 | |
| 3 | Colo-Colo | 2 | |
| 4 | Unión San Felipe | 2 |
| Rank | Team | Points | |
| 1 | Universidad Católica | 6 | |
|---|---|---|---|
| 2 | Rangers | 3 | |
| 3 | O'Higgins | 2 | |
| 4 | Deportes Valdivia | 1 |
| Rank | Team | Points | |
| 1 | Huachipato | 4 (+3) | |
|---|---|---|---|
| 2 | Naval | 4 (+2) | |
| 3 | Deportes Concepción | 3 | |
| 4 | Fernández Vial | 1 |
| width=190 | Home team | width=80 | Score | width=190 | Away team |
|---|---|---|---|---|---|
| Deportes La Serena | 1–3 | Unión Española | |||
| Universidad Católica | 2–0 | Naval | |||
| Everton | 2–0 | Cobreloa | |||
| Huachipato | 1–0 | Rangers |
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