Round: 44 Ground: Clay
| ITF Bolivia F3 | 2016/11/22 21:20 | Fabrizio Ornago v Gustavo De O Cruz | 7-6,6-0 |
| ITF Bolivia F3 Qual | 2016/11/20 14:00 | Gustavo De O Cruz v Alan Postay | 6-4,6-2 |
| ITF Bolivia F2 Qual | 2016/11/13 14:00 | Gustavo De O Cruz v Nicolas Bacella | 3-6,6-3,3-6 |
| ITF Bolivia F1 | 2016/11/06 16:30 | Gustavo De O Cruz v Javier Gonzalez | 4-6,6-7 |
| Challenger Campinas Qual | 2016/10/01 14:20 | Gustavo De O Cruz v Andre Miele | 7-5,3-6,5-7 |
| Challenger Curitiba Qual | 2016/08/27 13:30 | Gustavo De O Cruz v Felipe Garla | 2-6,3-6 |
| ITF Brazil F4 | 2016/07/20 15:00 | Gustavo De O Cruz v Carlos E. Severino | 6-7,3-6 |
| ITF Brazil F4 Qual | 2016/07/17 14:30 | Gustavo De O Cruz v Victor Bertoldo | 6-2,7-5 |
| ITF Argentina F13 | 2016/11/08 12:30 | Franco D Aubone v Santiago Besada | 6-3,6-4 |
| ITF Argentina F13 | 2016/11/08 12:20 | Franco David Aubone v Santiago Besada | 6-3,6-4 |
| ITF Argentina F13 | 2016/11/06 16:15 | Santiago Sarudiansky v Santiago Besada | 5-7,4-6 |
| ITF Argentina F13 | 2016/11/05 12:00 | Santiago Besada v Javier Roldan | 6-3,6-3 |
| ITF Argentina F12 Qual | 2016/10/29 22:00 | R. Urzua-Rivera v Santiago Besada | 6-2,6-0 |
| ITF Argentina F12 Qual | 2016/10/28 22:00 | Santiago Besada v Nicolas Xiviller | 6-2,6-2 |
| ITF Argentina F11 | 2016/10/25 13:00 | Santiago Besada v Gonzalo Villanueva | 0-6,1-6 |
| ITF Argentina F11 Qual | 2016/10/24 12:00 | Ivan Dikenstein v Santiago Besada | 5-7,1-6 |