[4] O'Higgins 1-2 Union La Calera [13] 2020-01-25 00:00
Stadium: El Teniente Round: 1
Referee: Angelo Hermosilla Home Manager: Patricio Graff Away Manager: Juan Pablo Vojvoda
Head to Head
| Chile - Primera Division | 2019/09/29 23:00 | O'Higgins v Union La Calera | W | 3-1 |
| Chile - Primera Division | 2019/04/28 16:30 | Union La Calera v O'Higgins | L | 2-0 |
| Chile - Primera Division | 2018/07/30 00:00 | O'Higgins v Union La Calera | L | 2-3 |
| Chile - Primera Division | 2018/05/19 19:00 | Union La Calera v O'Higgins | L | 4-0 |
| Chile Clausura | 2016/01/15 22:30 | O'Higgins v Union La Calera | W | 4-0 |
| Chile Apertura | 2015/07/25 23:30 | Union La Calera v O'Higgins | L | 1-0 |
| Chile Clausura | 2015/01/02 23:00 | O'Higgins v Union La Calera | W | 2-1 |
| Chile Apertura | 2014/07/20 19:30 | Union La Calera v O'Higgins | W | 1-2 |
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