Round: 26 Ground: Clay
| ITF Brazil F2 | 2016/07/07 17:00 | Oscar Jose Gutierrez v Santos, Nicolas | 6-4,6-3 |
| 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 |
| Challenger Curitiba Qual | 2016/08/27 15:45 | Oscar Jose Gutierrez v Luis Britto | 6-2,6-4 |
| ITF Brazil F4 | 2016/07/21 16:20 | Telles, Leonardo v Oscar Jose Gutierrez | 1-6,6-1,6-4 |
| ITF Colombia F4 | 2016/10/04 17:00 | Mora, Daniel v Santos, Nicolas | 4-6,4-6 |
| Challenger Medellin | 2016/09/28 21:00 | Giraldo, Santiago v Santos, Nicolas | 6-3,6-3 |
| Challenger Medellin | 2016/09/27 17:25 | Santos, Nicolas v Hernandez Ramirez, Sergio Luis | 4-6,6-2,6-1 |
| Others | 2016/09/25 18:15 | Santanna, B. v Santos, Nicolas | 4-6,6-1,5-7 |
| Others | 2016/09/24 20:10 | Santos, Nicolas v Juan Pablo Varillas | 7-6,6-3 |
| Challenger Medellin | 2016/09/24 16:20 | Santos, Nicolas v Giraldo Restrepo, Diego Alejandro | 6-2,6-2 |
| Challenger Curitiba Qual | 2016/08/28 18:15 | Mina, Gianni v Santos, Nicolas | 6-0,6-2 |
| Challenger Curitiba Qual | 2016/08/27 18:30 | Matos, Rafael v Santos, Nicolas | 6-4,3-6,2-6 |