| ITF Chile F6 | 2014/10/16 14:00 | Jose Pereira v Jorge Montero | 6-2,6-3 |
| ITF Chile F6 | 2014/10/14 15:40 | David Fleming v Jorge Montero | 4-6,4-6 |
| ITF Chile F5 | 2014/10/09 16:15 | Jorge Montero v Wilson Leite | 3-6,6-3,2-6 |
| ITF Chile F5 | 2014/10/08 14:55 | Jorge Montero v Alan Kohen | 4-6,7-6,6-3 |
| ITF Chile F5 | 2014/10/07 18:30 | Cristobal S-Corvalan v Jorge Montero | 3-6,2-6 |
| ITF Chile F1 | 2014/09/30 18:10 | Cristobal S-Corvalan v Jorge Montero | 5-7,7-6,6-2 |
| ITF Switzerland F5 | 2014/08/27 11:15 | Pascal Meis v Jorge Montero | 6-2,3-6,6-4 |
| ITF Switzerland F5 | 2014/08/26 15:55 | Johan Nikles v Jorge Montero | 4-6,1-6 |
| ITF Chile F7 | 2014/11/15 14:30 | Bruno L F Ureta v Javier Naser | 4-6,4-6 |