Round: 44 Ground: Clay
| ITF Chile F6 | 2016/12/04 15:00 | Leonardo Aboian v de Oliveira Cruz, Gustavo | 6-3,6-4 |
| ITF Chile F5 | 2016/12/11 15:00 | Fleming, David v Leonardo Aboian | 6-7,5-7 |
| ITF Chile F6 | 2016/12/07 16:30 | Malla, Bastian v Leonardo Aboian | 6-4,6-1 |
| ITF Chile F6 | 2016/12/06 14:00 | Leonardo Aboian v Hernandez Rojas, Diego Nicolas | 6-2,6-0 |
| ITF Chile F6 | 2016/12/04 15:00 | Leonardo Aboian v de Oliveira Cruz, Gustavo | 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 | Erhardt, Gaston v Leonardo Aboian | 2-6,1-6 |
| ITF Argentina F13 | 2016/11/05 12:00 | Martin, Juan 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 de Oliveira Cruz, Gustavo | 6-3,6-4 |
| ITF Chile F6 | 2016/12/03 14:00 | Papic, Nikolas v de Oliveira Cruz, Gustavo | 2-6,1-6 |
| ITF Chile F5 | 2016/11/27 16:00 | de Oliveira Cruz, Gustavo v Besada, Santiago | 3-6,1-6 |
| ITF Bolivia F3 | 2016/11/22 21:20 | Ornago, Fabrizio v de Oliveira Cruz, Gustavo | 7-6,6-0 |
| ITF Bolivia F3 Qual | 2016/11/20 14:00 | de Oliveira Cruz, Gustavo v Postay, Alan | 6-4,6-2 |
| ITF Bolivia F2 Qual | 2016/11/13 14:00 | de Oliveira Cruz, Gustavo v Bacella, Nicolas | 3-6,6-3,3-6 |
| ITF Bolivia F1 | 2016/11/06 16:30 | de Oliveira Cruz, Gustavo v Gonzalez, Javier (Chl) | 4-6,6-7 |
| Challenger Campinas Qual | 2016/10/01 14:20 | de Oliveira Cruz, Gustavo v Miele, Andre | 7-5,3-6,5-7 |