Round: 44 Ground: Hardcourt outdoor
| ITF Brazil F3 | 2016/07/09 12:00 | Gustavo De O Cruz v Fabio Costa | 4-6,6-4,0-6 |
| ITF Brazil F2 | 2016/07/05 20:00 | Gustavo De O Cruz v Gabriel Alejandro Hidalgo | 5-7,3-6 |
| ITF Brazil F2 | 2016/07/03 17:45 | Gustavo De O Cruz v Felipe D'Annunzio | 6-0,6-1 |
| ITF Brazil F2 | 2016/07/02 14:30 | Gustavo De O Cruz v Pedro Gabriel Rodrigues | 6-4,6-2 |
| ITF Argentina F3 | 2016/03/14 12:00 | Victor Nunez v Gustavo De O Cruz | 4-6,6-2,6-3 |
| ITF Argentina F3 | 2016/03/13 15:30 | Alejo Vilaro v Gustavo De O Cruz | 2-6,7-6,4-6 |
| ITF Argentina F3 | 2016/03/12 16:30 | Gustavo De O Cruz v Gregorio Cordonnier | 7-6,6-3 |
| ITF Argentina F2 | 2016/03/08 13:00 | Hernan Casanova v Gustavo De O Cruz | 6-3,6-0 |
| ITF Brazil F2 | 2016/07/03 16:30 | Eduardo Ribeiro v Enrico dos Santos Lima | 4-6,6-4,6-4 |
| ITF Brazil F1 | 2016/06/25 13:00 | Gabriel Roveri Sidney v Enrico dos Santos Lima | 7-5,6-1 |