Home History
| Chile Cup | 2014/06/06 23:00 | Union Espanola v Union La Calera | W | 0-1 |
| Chile Cup | 2014/05/31 22:00 | Union La Calera v Everton de Vina | W | 4-1 |
| Chile Cup | 2014/05/28 23:00 | Union La Calera v Union San Felipe | L | 1-2 |
| Chile Cup | 2014/05/25 19:30 | Union San Felipe v Union La Calera | L | 3-1 |
| Chile Cup | 2014/05/21 00:00 | Everton de Vina v Union La Calera | L | 2-1 |
| Chile Cup | 2014/05/17 22:00 | Union La Calera v Union Espanola | L | 0-3 |
Away History
| Chile Cup | 2014/07/16 19:30 | San Luis Quillota v O'Higgins | W | 1-2 |
| Chile Cup | 2014/05/29 23:00 | Santiago Wanderers v O'Higgins | L | 2-0 |
| Chile Cup | 2014/05/25 19:30 | O'Higgins v Santiago Wanderers | L | 1-4 |
| Chile Super Cup | 2014/05/03 20:30 | O'Higgins v Deportes Iquique | W | 3-2 |