Round: 62 Ground: Clay
| Challenger Campinas Qual | 2016/10/01 14:20 | Gustavo De O Cruz v Αντρέ Μίλε | 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 Brazil F4 Qual | 2016/07/16 16:30 | Gustavo De O Cruz v Enrico dos Santos Lima | 6-0,6-4 |
| 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 Γκαμπριέλ Αλεχάντρο Χιντάλγκο | 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 Bolivia F1 | 2016/11/05 16:30 | Χαβιέρ Γκονζάλεζ v Leonardo Reami Da Cunha | 4-6,6-4,6-1 |