Round: 25 Ground: Clay
| Challenger Cali 2 Qual | 2016/07/03 14:30 | Jorge Panta v Juan Montes | 6-7,6-3,6-2 |
| ITF Colombia F3 Qual | 2016/06/27 17:10 | Luis Patino v Juan Montes | 6-1,4-6,6-3 |
| ITF Colombia F3 Qual | 2016/06/26 15:30 | Juan Montes v Juan Jose Mateus Rubiano | 6-3,6-1 |
| ITF Colombia F2 | 2016/06/19 15:00 | Roberto Cid Subervi v Juan Montes | 6-3,6-0 |
| ITF Colombia F1 | 2016/06/13 16:35 | Juan Montes v Camilo Andres Erazo | 5-7,3-6 |
| ITF Mexico F5 | 2016/05/29 19:00 | Luis Britto v Juan Montes | 2-6,7-5,6-4 |
| ITF Mexico F4 | 2016/05/22 16:30 | Rudy Richter v Juan Montes | 7-6,6-2 |
| ITF Mexico F3 | 2016/05/15 17:30 | Janis Podzus v Juan Montes | 6-7,7-5,6-4 |
| Challenger Medellin | 2016/09/27 17:25 | Nicolas Santos v Sergio Luis H Ramirez | 4-6,6-2,6-1 |
| ITF Mexico F3 | 2016/05/16 15:00 | Juan Manuel Benitez Chavarriaga v Sergio Luis H Ramirez | 6-3,1-6,6-2 |
| ITF Mexico F3 | 2016/05/15 17:30 | Alexander Merino v Sergio Luis H Ramirez | 7-6,6-7,1-6 |
| ITF Mexico F2 | 2016/05/09 16:00 | Juan Manuel Benitez Chavarriaga v Sergio Luis H Ramirez | 6-7,6-0,6-1 |
| ITF Colombia F5 | 2015/07/08 15:00 | Kevin King v Sergio Luis H Ramirez | 6-1,6-3 |
| ITF Colombia F5 | 2015/07/07 16:50 | Sergio Luis H Ramirez v Tomas Builes | 3-6,6-4,6-4 |
| ITF Colombia F4 | 2014/08/24 15:00 | Daniel Mora v Sergio Luis H Ramirez | 2-6,6-4,7-5 |
| ITF Colombia F3 | 2014/08/18 18:15 | Sergio Luis H Ramirez v Jose Daniel Bendeck | 4-6,2-6 |