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