Round: 25 Ground: Clay
| ITF Belgium F3 | 2016/06/28 09:15 | Jakob Johansson-Holm v Caio Silva | 6-3,7-6 |
| ITF Spain F17 | 2016/06/16 14:00 | Caio Silva v Remi Boutillier | 0-6,2-6 |
| ITF Spain F17 | 2016/06/14 14:00 | Caio Silva v Diego-Jose Manrique-Velazquez | 1-6,6-3,6-4 |
| ITF Bosnia and Herzegovina F2 | 2016/05/17 12:05 | Caio Silva v Tomislav Jotovski | 1-6,3-6 |
| ITF Bosnia and Herzegovina F1 | 2016/05/11 09:30 | Caio Silva v Danylo Kalenichenko | 3-6,3-6 |
| ITF Portugal F4 | 2016/05/04 11:00 | Tiago Cacao v Caio Silva | 6-1,7-6 |
| ITF Russia F8 | 2015/09/08 07:00 | Caio Silva v Ricardo Rodriguez-Pace | 1-6,2-6 |
| ITF Russia F7 | 2015/08/31 07:00 | Vitaly Kozyukov v Caio Silva | 7-6,3-6,7-6 |
| ITF Austria F1 | 2016/07/03 12:15 | Goncalo Oliveira v Maxime Guichoud | 6-1,6-1 |
| ITF Austria F1 | 2016/07/02 08:00 | Goncalo Oliveira v Johannes Bangratz | 6-3,6-4 |
| ITF Italy F18 | 2016/06/29 16:10 | Davide Galoppini v Goncalo Oliveira | 4-6,6-4,6-4 |
| ITF Italy F18 | 2016/06/28 15:00 | Federico Ottolini v Goncalo Oliveira | 3-6,3-6 |
| Challenger Milan Qual | 2016/06/19 09:30 | Goncalo Oliveira v Lorenzo Sonego | 1-6,2-6 |
| Challenger Perugia Qual | 2016/06/11 08:30 | Ricardo Rodriguez-Pace v Goncalo Oliveira | 5-7,7-5,7-6 |
| ITF Italy F14 | 2016/06/09 08:00 | Adelchi Virgili v Goncalo Oliveira | 7-6,3-6,6-3 |
| ITF Italy F14 | 2016/06/07 12:30 | Mateo Nicolas Martinez v Goncalo Oliveira | 6-7,2-6 |