Round: 44 Ground: Clay
| ITF Italy F27 | 2016/08/29 09:00 | Tobias Simon v Riccardo Roberto | 6-1,6-2 |
| ITF Italy F27 | 2016/08/28 08:00 | Riccardo Roberto v Marco Mosciatti | 6-4,7-5 |
| ITF Italy F27 | 2016/08/27 11:00 | Francesco Moncagatto v Riccardo Roberto | 6-2,6-7,2-6 |
| ITF Italy F25 Qual | 2016/08/15 07:30 | Andres Gabriel Ciurletti v Riccardo Roberto | 6-1,7-6 |
| ITF Italy F25 Qual | 2016/08/13 08:00 | Riccardo Roberto v Alessandro Ragazzi | 6-0,6-3 |
| 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 Switzerland F5 Qual | 2016/08/27 09:30 | Louroi Martinez v Michele Longo | 6-3,6-3 |
| ITF Italy F26 Qual | 2016/08/21 09:00 | Antonio Zucca v Michele Longo | 3-6,6-3,7-5 |
| ITF Italy F26 Qual | 2016/08/20 08:00 | Michele Longo v Filippo Miliani | 6-2,6-0 |
| ITF Italy F25 | 2016/08/15 15:00 | Tomas Barrios Vera v Michele Longo | 6-2,6-2 |
| ITF Austria F5 Qual | 2016/08/08 08:00 | Jakob Schnaitter v Michele Longo | 4-6,6-1,6-1 |
| ITF Austria F5 Qual | 2016/08/07 08:30 | Michele Longo v Matteo Curci | 6-7,6-3,6-1 |
| ITF Austria F5 Qual | 2016/08/06 08:30 | Francesco Cano v Michele Longo | 5-7,3-6 |
| Challenger Cortina Qual | 2016/07/30 09:25 | Michele Longo v Walter Trusendi | 0-6,1-6 |