Head to Head
| 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 |
Home History
| Chile Apertura | 2016/09/12 23:30 | Audax Italiano v Union Espanola | L | 3-1 |
| Chile Apertura | 2016/08/27 23:00 | Union Espanola v O'Higgins | D | 1-1 |
| Chile Apertura | 2016/08/19 22:30 | Everton de Vina v Union Espanola | D | 1-1 |
| Chile Apertura | 2016/08/14 18:30 | Huachipato v Union Espanola | D | 2-2 |
| Chile Apertura | 2016/08/07 00:30 | Union Espanola v Universidad de Concepcion | W | 3-0 |
| Chile Apertura | 2016/07/31 19:30 | Colo Colo v Union Espanola | W | 1-2 |
| Chile Cup | 2016/07/16 21:30 | Union Espanola v Magallanes | D | 4-4 |
| Chile Cup | 2016/07/10 16:00 | Magallanes v Union Espanola | W | 1-2 |
Away History
| Chile Apertura | 2016/09/11 15:00 | O'Higgins v Huachipato | W | 2-0 |
| Chile Apertura | 2016/08/27 23:00 | Union Espanola v O'Higgins | D | 1-1 |
| Chile Apertura | 2016/08/20 18:00 | O'Higgins v Deportes Temuco | W | 1-0 |
| Copa Sudamericana | 2016/08/16 23:30 | O'Higgins v Montevideo Wanderers | L | 4-5 |
| Chile Apertura | 2016/08/13 16:00 | Deportes Iquique v O'Higgins | D | 1-1 |
| Copa Sudamericana | 2016/08/11 00:00 | Montevideo Wanderers v O'Higgins | D | 0-0 |
| Chile Apertura | 2016/08/06 00:30 | O'Higgins v Universidad Catolica | D | 1-1 |
| Chile Apertura | 2016/07/30 00:00 | San Luis Quillota v O'Higgins | W | 0-1 |