[16] Santiago Wanderers 1-2 Union La Calera [5] 2021-04-11 21:30
Stadium: Estadio Elias Figueroa Brander Round: 3
Referee: Eduardo Gamboa Latourniere Home Manager: Ronald Hugo Fuentes Nunez Away Manager: Juan Pablo Vojvoda
Head to Head
| Chile Primera Division | 2021/01/02 22:15 | Union La Calera v Santiago Wanderers | L | 3-0 |
| Chile Primera Division | 2020/10/15 16:30 | Santiago Wanderers v Union La Calera | L | 0-3 |
| Chile Play-Offs | 2017/12/21 22:00 | Santiago Wanderers v Union La Calera | L | 4-6 |
| Chile Play-Offs | 2017/12/14 22:00 | Union La Calera v Santiago Wanderers | W | 0-1 |
| Chile Clausura | 2016/02/29 22:30 | Union La Calera v Santiago Wanderers | D | 3-3 |
| Chile Apertura | 2015/09/26 21:00 | Santiago Wanderers v Union La Calera | W | 1-0 |
| Chile Cup | 2015/08/02 15:00 | Santiago Wanderers v Union La Calera | W | 4-1 |
| Chile Cup | 2015/07/15 22:00 | Union La Calera v Santiago Wanderers | D | 2-2 |
| Chile Clausura | 2015/04/25 20:30 | Santiago Wanderers v Union La Calera | W | 4-2 |
| Chile Apertura | 2014/11/30 21:00 | Union La Calera v Santiago Wanderers | W | 0-1 |