Round: 27 Ground: Clay
| ITF Chile F5 | 2016/11/30 15:00 | Facundo Juarez v Montero, Jorge | 6-7,3-6 |
| ITF Chile F5 | 2016/11/28 16:30 | Montero, Jorge v Pereira, Miguel Fernando | 6-4,6-2 |
| ITF Colombia F8 | 2016/11/22 16:35 | Montero, Jorge v Juan Sebastian Gomez | 4-6,4-6 |
| 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 Chile F5 | 2016/11/30 14:40 | Ameal, Juan Ignacio v Malla, Bastian | 4-6,2-6 |
| ITF Chile F5 | 2016/11/29 21:10 | Vernier, Michel v Malla, Bastian | 4-6,4-6 |
| Montevideo, Uruguay | 2016/11/16 17:00 | Nicolas Kicker v Malla, Bastian | 6-1,6-1 |
| Montevideo, Uruguay | 2016/11/14 19:00 | Malla, Bastian v Maresca, Santiago | 6-3,6-4 |
| Challenger Bogota Qual | 2016/11/05 17:40 | Malla, Bastian v Lopes, Tiago | 3-6,1-6 |
| Challenger Guayaquil Qual | 2016/10/30 17:00 | Linzer, Michael v Malla, Bastian | 6-2,3-6,5-7 |
| Challenger Guayaquil Qual | 2016/10/29 21:45 | Malla, Bastian v Nicolas Jarry | 6-4,1-6,7-5 |
| Challenger Lima Qual | 2016/10/22 15:30 | Sorgi, Joao Pedro v Malla, Bastian | 3-6,6-4,6-3 |