Round: 25 Ground: Hardcourt outdoor
| ITF Colombia F7 | 2016/11/14 17:30 | Montero, Jorge v Juan Sebastian Gomez | 6-4,1-6,2-6 |
| ITF Colombia F3 | 2016/06/28 14:30 | Juan Sebastian Gomez v Montero, Jorge | 6-4,6-1 |
| ITF Colombia F2 | 2015/05/18 17:55 | Juan Sebastian Gomez v Montero, Jorge | 2-6,7-6,3-6 |
| ITF Colombia F7 | 2016/11/14 17:30 | Montero, Jorge v Juan Sebastian Gomez | 6-4,1-6,2-6 |
| Challenger Guayaquil Qual | 2016/10/29 17:25 | Montero, Jorge v Nicolas Jarry | 5-7,3-6 |
| ITF Ecuador F3 | 2016/10/24 21:50 | Montero, Jorge v Zukas, Matias | 3-6,3-6 |
| Challenger Santiago 2 Qual | 2016/10/16 16:00 | Montero, Jorge v Hidalgo, Gabriel Alejandro | 4-6,6-7 |
| Challenger Santiago 2 Qual | 2016/10/15 13:40 | Montero, Jorge v Nicolas Bruna | 6-1,6-1 |
| ITF Colombia F4 | 2016/10/06 16:30 | Montero, Jorge v Hocevar, Ricardo | 6-4,3-6,4-6 |
| ITF Colombia F4 | 2016/10/04 18:45 | Mantilla, Felipe v Montero, Jorge | 0-6,6-4,6-7 |
| Others | 2016/09/24 20:20 | Santanna, B. v Montero, Jorge | 6-3,4-6,6-3 |
| ITF Colombia F7 | 2016/11/19 19:00 | Juan Sebastian Gomez v Juan Pablo Varillas | 6-7,6-1,6-3 |
| ITF Colombia F7 | 2016/11/18 17:20 | Santos, Nicolas v Juan Sebastian Gomez | 6-2,4-6,4-6 |
| ITF Colombia F7 | 2016/11/17 16:30 | Gomez, Lucas v Juan Sebastian Gomez | 4-6,3-6 |
| ITF Colombia F7 | 2016/11/16 15:00 | Serrano, Sebastian v Juan Sebastian Gomez | 6-2,5-7,5-7 |
| ITF Colombia F7 | 2016/11/14 17:30 | Montero, Jorge v Juan Sebastian Gomez | 6-4,1-6,2-6 |
| Challenger Bogota Qual | 2016/11/05 15:00 | Tomas Barrios Vera v Juan Sebastian Gomez | 6-0,6-2 |
| ITF Colombia F6 | 2016/10/20 15:00 | Juan Sebastian Gomez v Santos, Nicolas | 6-7,6-1,4-6 |
| ITF Colombia F6 | 2016/10/17 19:00 | Juan Sebastian Gomez v Hernandez Ramirez, Sergio Luis | 6-1,7-6 |