Round: 62 Ground: Clay
| ITF Italy F13 | 2016/05/29 07:30 | Goncalo Oliveira v Federico Bertuccioli | 6-2,6-4 |
| Challenger Vicenza Qual | 2016/05/22 12:40 | Stefano Napolitano v Goncalo Oliveira | 6-4,6-1 |
| Challenger Vicenza Qual | 2016/05/21 09:45 | Goncalo Oliveira v Robin Stanek | 6-2,6-4 |
| Challenger Mestre Qual | 2016/05/15 09:00 | Goncalo Oliveira v Daniel Masur | 3-6,0-6 |
| Challenger Mestre Qual | 2016/05/14 08:00 | Goncalo Oliveira v Marc Giner | 6-1,6-2 |
| Challenger Aix en Provence Qual | 2016/04/30 12:30 | Goncalo Oliveira v Gregoire Jacq | 1-6,4-6 |
| ITF France F9 | 2016/04/25 10:30 | Goncalo Oliveira v Andreas Beck | 6-4,4-6,6-7 |
| ITF Italy F4 | 2016/04/06 08:00 | Goncalo Oliveira v Elie Rousset | 7-6,2-6,4-6 |
| ITF Italy F13 | 2016/05/29 07:30 | Cristiano Russo v Riccardo Roberto | 5-7,6-4,2-6 |
| ITF Italy F13 | 2016/05/28 08:30 | Riccardo Roberto v Gil Uwe Grund | 6-2,7-6 |
| ITF Italy F11 Qual | 2016/05/16 14:55 | Cristian Carli v Riccardo Roberto | 6-2,6-3 |
| ITF Italy F11 Qual | 2016/05/16 10:10 | Riccardo Roberto v Augusto Virgili | 7-6,6-3 |
| ITF Italy F7 | 2016/04/18 08:00 | Mirko Cutuli v Riccardo Roberto | 6-2,6-2 |
| ITF Italy F6 | 2016/04/11 10:00 | Riccardo Roberto v Luca Giacomini | 1-6,3-6 |
| ITF Italy F6 Qual | 2016/04/10 08:00 | Davide Galoppini v Riccardo Roberto | 7-5,1-6,6-7 |
| ITF Croatia F4 Qual | 2016/03/20 14:00 | Pietro Licciardi v Riccardo Roberto | 6-2,6-4 |