Round: 26 Ground: Clay
| Challenger Curitiba | 2016/08/31 17:35 | Igor Marcondes v Maximiliano Estevez | 6-4,6-1 |
| Challenger Cali 2 | 2016/07/05 16:30 | Jose Hernandez-Fernandez v Maximiliano Estevez | 6-0,6-2 |
| ITF Colombia F3 | 2016/06/29 17:45 | Maximiliano Estevez v Cristian Rodriguez | 1-6,2-6 |
| ITF Colombia F3 | 2016/06/28 18:05 | Maximiliano Estevez v Carlos Salamanca | 6-2,6-4 |
| ITF Colombia F2 | 2016/06/20 18:05 | Maximiliano Estevez v Gonzalo Villanueva | 4-6,3-6 |
| ITF Argentina F9 | 2016/06/01 22:00 | Maximiliano Estevez v Eduardo Agustin Torre | 7-5,7-5 |
| ITF Argentina F9 | 2016/05/30 22:00 | Maximiliano Estevez v Gabriel Alejandro Hidalgo | 6-3,6-4 |
| ITF Argentina F8 | 2016/05/24 22:00 | Maximiliano Estevez v Igor Marcondes | 2-6,5-7 |
| Challenger Barranquilla | 2016/09/06 17:40 | Juan Carlos Saez v Rogerio Dutra Silva | 0-6,4-6 |
| US Open | 2016/08/29 15:00 | Rogerio Dutra Silva v Marin Cilic | 4-6,5-7,1-6 |
| ATP Kitzbuhel | 2016/07/19 12:35 | Dusan Lajovic v Rogerio Dutra Silva | 7-6,6-1 |
| Davis Cup | 2016/07/15 19:00 | Rogerio Dutra Silva v Emilio Gomez | 6-4,5-7,0-6,4-6 |
| Wimbledon | 2016/06/27 10:30 | Nicolas Almagro v Rogerio Dutra Silva | 6-3,7-6,5-7,3-6,6-3 |
| Challenger Milan Qual | 2016/06/23 10:00 | Rogerio Dutra Silva v Arthur De Greef | 7-6,2-6,3-6 |
| Challenger Milan Qual | 2016/06/21 13:35 | Rogerio Dutra Silva v Andrea Basso | 6-0,6-2 |
| Challenger Perugia | 2016/06/17 09:30 | Rogerio Dutra Silva v Blaz Rola | 6-7,2-6 |