Head to Head
| Chile Primera Division | 2024/04/26 23:00 | O'Higgins v Union Espanola | D | 2-2 |
| Chile Primera Division | 2023/11/12 23:00 | Union Espanola v O'Higgins | D | 3-3 |
| Chile Primera Division | 2023/04/30 22:00 | O'Higgins v Union Espanola | D | 1-1 |
| Chile Primera Division | 2022/10/08 23:00 | Union Espanola v O'Higgins | D | 0-0 |
| Chile Cup | 2022/08/22 00:00 | Union Espanola v O'Higgins | W | 1-0 |
| Chile Cup | 2022/08/18 00:30 | O'Higgins v Union Espanola | W | 1-3 |
| Chile Primera Division | 2022/05/07 19:00 | O'Higgins v Union Espanola | D | 2-2 |
| Chile Primera Division | 2021/10/03 23:30 | Union Espanola v O'Higgins | W | 3-2 |
| Chile Primera Division | 2021/05/08 00:00 | O'Higgins v Union Espanola | W | 1-4 |
| Chile Primera Division | 2020/11/24 00:30 | Union Espanola v O'Higgins | L | 0-2 |
| Chile Primera Division | 2020/02/24 23:30 | O'Higgins v Union Espanola | W | 1-3 |
| Chile Primera Division | 2019/08/23 23:30 | Union Espanola v O'Higgins | L | 0-1 |
| Chile Primera Division | 2019/03/30 23:30 | O'Higgins v Union Espanola | W | 0-2 |
| Chile Primera Division | 2018/08/25 23:00 | O'Higgins v Union Espanola | D | 1-1 |
| Chile Primera Division | 2018/04/08 23:00 | Union Espanola v O'Higgins | W | 2-0 |
| Chile Apertura | 2017/08/12 00:00 | O'Higgins v Union Espanola | W | 0-2 |
| Chile Clausura | 2017/02/11 21:00 | O'Higgins v Union Espanola | L | 2-0 |
| Chile Apertura | 2016/12/17 22:00 | Union Espanola v O'Higgins | W | 5-3 |
| Chile Cup | 2016/09/21 21:30 | O'Higgins v Union Espanola | W | 1-2 |
| Chile Cup | 2016/09/15 21:30 | Union Espanola v O'Higgins | W | 4-0 |
| Chile Apertura | 2016/08/27 23:00 | Union Espanola v O'Higgins | D | 1-1 |
| Chile Clausura | 2016/03/18 23:30 | O'Higgins v Union Espanola | D | 0-0 |
| Chile Apertura | 2015/10/24 15:30 | Union Espanola v O'Higgins | L | 1-2 |
| Chile Clausura | 2015/02/22 00:00 | Union Espanola v O'Higgins | L | 1-2 |
| Chile Apertura | 2014/09/13 21:00 | O'Higgins v Union Espanola | W | 1-3 |