Round: 44 Ground: Clay
| ITF Italy F14 Qual | 2016/06/05 11:50 | Toby Martin v Riccardo Roberto | 6-3,6-3 |
| ITF Italy F14 Qual | 2016/06/04 10:45 | Riccardo Roberto v Facundo Jofre | 7-5,6-2 |
| ITF Italy F13 | 2016/05/30 08:00 | Goncalo Oliveira v Riccardo Roberto | 6-1,6-3 |
| 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 |
| Challenger Cortina Qual | 2016/07/30 08:00 | Alessandro Ragazzi v Augusto Virgili | 3-6,7-5,6-7 |
| ITF Croatia F3 | 2016/03/13 12:30 | Alessandro Ragazzi v Paul Woerner | 2-6,3-6 |
| ITF Croatia F3 | 2016/03/12 09:00 | Marco De Rosa v Alessandro Ragazzi | 3-6,1-6 |
| ITF Croatia F2 | 2016/03/06 08:30 | Alessandro Ragazzi v Vladimir Filip | 6-3,6-3 |
| ITF Tunisia F8 | 2016/02/28 08:30 | Filipp Kekercheni v Alessandro Ragazzi | 6-1,6-1 |