Round: 25 Ground: Hardcourt outdoor
| Challenger Granby Qual | 2016/07/30 18:00 | Juan Carlos Aguilar v Raleigh Smith | 1-6,6-1,2-6 |
| ITF Dominican Republic F3 | 2015/12/13 14:00 | Juan Carlos Aguilar v Alexander Donski | 6-7,2-6 |
| ITF Dominican Republic F2 | 2015/12/08 15:30 | Juan Carlos Aguilar v Winston Lin | 2-6,3-6 |
| ITF Dominican Republic F2 | 2015/12/07 15:45 | Juan Carlos Aguilar v Conor Berg | 7-5,6-2 |
| ITF Dominican Republic F2 | 2015/12/06 14:00 | Juan Carlos Aguilar v Masaki Osafune | 7-5,6-3 |
| ITF Dominican Republic F1 | 2015/12/02 16:50 | Juan Carlos Aguilar v Benjamin Hannestad | 4-6,4-6 |
| ITF Dominican Republic F1 | 2015/12/01 21:45 | Peter Bertran v Juan Carlos Aguilar | 4-6,5-7 |
| ITF Bolivia F3 | 2015/09/23 20:45 | Juan Carlos Aguilar v Ryusei Makiguchi | 4-6,5-7 |
| ITF Canada F7 | 2016/09/11 15:30 | Frank Dancevic v Ivan Endara | 7-6,7-6 |
| ITF Canada F7 | 2016/09/10 16:30 | Alexander Ritschard v Ivan Endara | 7-6,4-6,3-6 |
| ITF Canada F7 | 2016/09/09 16:00 | Ivan Endara v David Volfson | 6-3,2-6,6-1 |
| ITF Canada F7 | 2016/09/08 16:00 | Ivan Endara v Manuel Sanchez | 4-6,6-4,6-2 |
| ITF Canada F7 | 2016/09/06 19:00 | Takanyi Garanganga v Ivan Endara | 6-2,2-6,1-6 |
| 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 |