Round: 26 Ground: Clay
| ITF Italy F14 | 2016/06/08 14:55 | Jacopo Stefanini v Gianluca Di Nicola | 6-1,6-3 |
| ITF Italy F34 | 2016/10/17 08:00 | Gianluca Di Nicola v Umberto Maria Giovannini | 6-1,6-2 |
| ITF Italy F32 | 2016/10/05 11:20 | Corentin Denolly v Gianluca Di Nicola | 6-3,6-7,6-3 |
| ITF Italy F32 | 2016/10/04 07:30 | Riccardo Sinicropi v Gianluca Di Nicola | 6-7,2-6 |
| ITF Italy F31 | 2016/09/28 09:40 | Gianluca Di Nicola v Francesco Picco | 6-7,6-7 |
| ITF Italy F31 | 2016/09/26 13:00 | Gianluca Di Nicola v Umberto Maria Giovannini | 4-6,6-3,6-2 |
| ITF Italy F31 Qual | 2016/09/25 07:30 | Gianluca Di Nicola v Jordi Walder | 6-1,6-3 |
| ITF Italy F30 | 2016/09/22 10:50 | Walter Trusendi v Gianluca Di Nicola | 6-4,6-2 |
| ITF Italy F30 | 2016/09/21 09:25 | Gianluca Di Nicola v Filippo Leonardi | 6-2,6-3 |
| ITF Italy F34 | 2016/10/18 10:10 | Jacopo Stefanini v Petru-Alexandru Luncanu | 6-3,6-2 |
| ITF Italy F33 | 2016/10/11 11:05 | Jacopo Stefanini v Daniel Altmaier | 2-6,6-7 |
| ITF Italy F32 | 2016/10/05 07:30 | Yannick Maden v Jacopo Stefanini | 6-3,6-0 |
| ITF Italy F32 | 2016/10/04 07:30 | Jacopo Stefanini v Umberto Maria Giovannini | 6-2,6-0 |
| Challenger Rome 2 Qual | 2016/09/25 11:30 | Jacopo Stefanini v Mikael Ymer | 2-6,3-6 |
| Challenger Rome 2 Qual | 2016/09/24 13:30 | Cristian Rodriguez v Jacopo Stefanini | 2-6,3-6 |
| Challenger Rome 2 Qual | 2016/09/24 10:00 | Jacopo Stefanini v Luigi Sorrentino | 6-0,2-6,6-4 |
| ITF Italy F29 | 2016/09/17 08:30 | Jacopo Stefanini v Gabriel Alejandro Hidalgo | 6-2,6-2 |