Round: 44 Ground: Clay
| ITF Chile F6 | 2016/12/04 15:00 | Leonardo Aboian v Gustavo De O Cruz | 6-3,6-4 |
| ITF Chile F5 | 2016/12/11 15:00 | David Fleming v Leonardo Aboian | 6-7,5-7 |
| ITF Chile F6 | 2016/12/07 16:30 | Bastian Malla v Leonardo Aboian | 6-4,6-1 |
| ITF Chile F6 | 2016/12/06 14:00 | Leonardo Aboian v Diego N H Rojas | 6-2,6-0 |
| ITF Chile F6 | 2016/12/04 15:00 | Leonardo Aboian v Gustavo De O Cruz | 6-3,6-4 |
| ITF Argentina F13 | 2016/11/07 13:25 | Facundo Juarez v Leonardo Aboian | 6-4,5-7,6-0 |
| ITF Argentina F13 | 2016/11/06 16:15 | Gaston Erhardt v Leonardo Aboian | 2-6,1-6 |
| ITF Argentina F13 | 2016/11/05 12:00 | Juan Martin v Leonardo Aboian | 5-7,6-7 |
| ITF Argentina F12 Qual | 2016/10/29 22:00 | Leonardo Aboian v Sebastian Baez | 3-6,3-6 |
| ITF Chile F6 | 2016/12/04 15:00 | Leonardo Aboian v Gustavo De O Cruz | 6-3,6-4 |
| ITF Chile F6 | 2016/12/03 14:00 | Nikolas Papic v Gustavo De O Cruz | 2-6,1-6 |
| ITF Chile F5 | 2016/11/27 16:00 | Gustavo De O Cruz v Santiago Besada | 3-6,1-6 |
| 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 |