Round: 26 Ground: Clay
| ITF Colombia F5 | 2016/10/11 15:40 | Oscar Jose Gutierrez v de Marco, Nicolas | 6-4,6-1 |
| ITF Colombia F4 | 2016/10/06 15:00 | Oscar Jose Gutierrez v Santos, Nicolas | 3-6,7-5,6-7 |
| ITF Colombia F4 | 2016/10/04 21:05 | Juan Sebastian Gomez v Oscar Jose Gutierrez | 3-6,6-4,2-6 |
| Challenger - Santos | 2016/09/19 16:00 | Gonzalez, Maximo v Oscar Jose Gutierrez | 6-1,6-3 |
| Challenger Santos Qual | 2016/09/18 14:00 | Oscar Jose Gutierrez v Santos, Luiz Eduardo | 6-1,6-2 |
| Challenger Curitiba | 2016/08/31 16:50 | Oscar Jose Gutierrez v Ghem, Andre | 2-6,0-6 |
| Challenger Curitiba Qual | 2016/08/28 18:05 | Oscar Jose Gutierrez v Lopes, Tiago | 4-6,6-3,5-4 |
| Challenger Curitiba Qual | 2016/08/28 15:35 | Oscar Jose Gutierrez v Lopes, Tiago | 4-6,6-3,6-4 |
| ITF Colombia F5 | 2016/10/11 15:00 | Alvarez-Guzman, Mauricio v Montes, Juan | 2-6,2-6 |
| ITF Colombia F5 | 2016/10/10 15:30 | Montes, Juan v Zuluaga Gaviria, Barlaham | 6-2,6-4 |
| ITF Colombia F5 | 2016/10/09 16:00 | Treyz, Beauregard v Montes, Juan | 1-6,0-6 |
| ITF Colombia F4 | 2016/10/04 15:00 | Montes, Juan v Hernandez Ramirez, Sergio Luis | 5-7,5-7 |
| Challenger Cali 2 Qual | 2016/07/03 14:30 | Panta Herreros, Jorge Brian v Montes, Juan | 6-7,6-3,6-2 |
| ITF Colombia F3 Qual | 2016/06/27 17:10 | Patino, Luis v Montes, Juan | 6-1,4-6,6-3 |
| ITF Colombia F3 Qual | 2016/06/26 15:30 | Montes, Juan v Mateus Rubiano, Juan Jose | 6-3,6-1 |
| ITF Colombia F2 | 2016/06/19 15:00 | Roberto Cid Subervi v Montes, Juan | 6-3,6-0 |