Round: 27 Ground: Hardcourt outdoor
| Challenger Cali 2 Qual | 2016/07/03 19:50 | Luis Patino v Ivan Endara | 6-4,6-4 |
| ITF Colombia F3 | 2016/06/28 16:40 | Christopher Diaz-Figueroa v Ivan Endara | 4-6,6-3,6-3 |
| ITF Mexico F3 | 2016/05/16 22:00 | Ivan Endara v Mico Santiago | 3-6,3-6 |
| ITF Mexico F1 | 2016/05/05 19:30 | Hans Hach Verdugo v Ivan Endara | 3-6,6-3,2-6 |
| ITF Mexico F1 | 2016/05/03 16:00 | Luis Britto v Ivan Endara | 0-6,2-6 |
| Challenger Leon Qual | 2016/03/27 21:30 | Juan Ignacio Londero v Ivan Endara | 5-7,6-4,6-1 |
| Challenger Leon Qual | 2016/03/27 17:30 | Ivan Endara v Alejandro Mendoza | 6-3,6-2 |
| Challenger San Luis Potosi Qual | 2016/03/21 16:30 | Ivan Endara v Agustin Velotti | 6-7,2-6 |
| ITF Brazil F4 | 2016/07/21 16:20 | Leonardo Civita-Telles v Oscar Jose Gutierrez | 1-6,6-1,6-4 |
| ITF Brazil F4 | 2016/07/19 18:35 | Facundo Jofre v Oscar Jose Gutierrez | 1-6,3-6 |
| ITF Brazil F3 | 2016/07/14 17:00 | Rafael Matos v Oscar Jose Gutierrez | 7-5,2-6,6-3 |
| ITF Brazil F3 | 2016/07/12 17:30 | Oscar Jose Gutierrez v Daniel Dutra Da Silva | 6-1,6-4 |
| ITF Brazil F2 | 2016/07/09 20:00 | Oscar Jose Gutierrez v Fernando Romboli | 4-6,3-6 |
| ITF Brazil F2 | 2016/07/08 20:00 | Oscar Jose Gutierrez v Rafael Matos | 6-4,2-6,6-1 |
| ITF Brazil F2 | 2016/07/07 17:00 | Oscar Jose Gutierrez v Nicolas Santos | 6-4,6-3 |
| ITF Brazil F2 | 2016/07/06 14:00 | Carlos E. Severino v Oscar Jose Gutierrez | 3-6,4-6 |