Round: 46 Ground: Clay
| Challenger Curitiba Qual | 2016/08/27 13:30 | de Oliveira Cruz, Gustavo v Assuncao Garla, Felipe | 2-6,3-6 |
| ITF Brazil F4 | 2016/07/20 15:00 | de Oliveira Cruz, Gustavo v Severino, Carlos Eduardo | 6-7,3-6 |
| ITF Brazil F4 Qual | 2016/07/17 14:30 | de Oliveira Cruz, Gustavo v Segantini Bertoldo, Victor | 6-2,7-5 |
| ITF Brazil F4 Qual | 2016/07/16 16:30 | de Oliveira Cruz, Gustavo v Lima, Enrico Dos Santos | 6-0,6-4 |
| ITF Brazil F3 | 2016/07/09 12:00 | de Oliveira Cruz, Gustavo v Costa, Fabio | 4-6,6-4,0-6 |
| ITF Brazil F2 | 2016/07/05 20:00 | de Oliveira Cruz, Gustavo v Hidalgo, Gabriel Alejandro | 5-7,3-6 |
| ITF Brazil F2 | 2016/07/03 17:45 | de Oliveira Cruz, Gustavo v D'Annunzio, Felipe | 6-0,6-1 |
| ITF Brazil F2 | 2016/07/02 14:30 | de Oliveira Cruz, Gustavo v Rodrigues, Pedro Gabriel | 6-4,6-2 |
| Challenger - Santos | 2016/09/20 16:30 | Miele, Andre v Neis, Fabricio | 1-6,1-6 |
| Challenger Curitiba Qual | 2016/08/28 13:30 | Miele, Andre v Neis, Fabricio | 6-7,1-6 |
| Challenger Curitiba Qual | 2016/08/27 15:15 | Miele, Andre v Rodrigues Girotto, Alexandre Gabriel | 6-2,6-0 |
| ITF Brazil F4 | 2016/07/22 14:00 | Miele, Andre v Severino, Carlos Eduardo | 3-6,6-7 |
| ITF Brazil F4 | 2016/07/20 15:25 | Miele, Andre v Spiering, Marvin Bernardo Becker | 6-2,4-6,6-1 |
| ITF Brazil F4 | 2016/07/18 15:15 | Miele, Andre v Luis Britto | 6-0,6-1 |
| ITF Brazil F3 | 2016/07/15 17:00 | Fernando Yamacita v Miele, Andre | 6-1,6-4 |
| ITF Brazil F3 | 2016/07/13 14:00 | Jofre, Facundo v Miele, Andre | 3-6,4-6 |