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 Latvia F1 | 2016/08/03 07:00 | Claudio Fortuna v David Volfson | 6-3,6-3 |
| ITF Latvia F1 | 2016/08/02 07:00 | Harrison Lombe v David Volfson | 0-6,0-6 |
| ITF Georgia F1 | 2016/07/28 10:40 | Baptiste Crepatte v David Volfson | 6-3,6-2 |
| ITF Lithuania F1 | 2016/07/19 10:15 | David Volfson v Pirmin Haenle | 6-7,2-6 |
| Challenger Winnipeg Qual | 2016/07/09 21:00 | David Volfson v Luke Bambridge | 3-6,3-6 |
| ITF Canada F5 | 2016/07/05 19:10 | David Volfson v Tim Kopinski | 6-1,4-6,3-6 |
| ITF USA F19 Qual | 2016/06/12 15:00 | David Volfson v Christian Lakoseljac | 3-6,4-6 |
| ITF USA F17 Qual | 2016/06/06 15:15 | David Volfson v Rowland Phillips | 4-6,6-7 |