Round: 54 Ground: Clay
| ITF Italy F22 Qual | 2016/07/24 08:00 | Alessandro Ceppellini v Lorenzo Papasidero | 6-3,3-6,4-6 |
| ITF Italy F21 | 2016/07/19 15:30 | Alessandro Ceppellini v Andrea Pellegrino | 3-6,2-6 |
| ITF Italy F20 Qual | 2016/07/09 07:30 | Alessandro Ceppellini v Daniele Chiurulli | 6-1,6-4 |
| ITF Italy F19 | 2016/07/06 14:05 | Juan Pablo Paz v Alessandro Ceppellini | 6-2,6-2 |
| ITF Italy F19 | 2016/07/04 09:00 | Pietro Licciardi v Alessandro Ceppellini | 6-4,4-6,5-7 |
| ITF Italy F19 | 2016/07/03 08:50 | Alessandro Cortegiani v Alessandro Ceppellini | 1-6,6-4,1-6 |
| ITF Italy F19 | 2016/07/02 11:05 | Riccardo Stiglich v Alessandro Ceppellini | 1-6,1-6 |
| ITF Italy F18 Qual | 2016/06/25 07:30 | Alessandro Coppini v Alessandro Ceppellini | 6-4,7-6 |
| 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 |