Round: 26 Ground: Clay
| ITF Italy F14 | 2016/06/06 15:00 | Ghedin, Nicola v Stefanini, Jacopo | 6-2,6-7,6-7 |
| ITF Italy F14 Qual | 2016/06/05 13:00 | Stefanini, Jacopo v Albertoni, Davide | 6-3,6-4 |
| ITF Italy F14 Qual | 2016/06/04 15:20 | Stefanini, Jacopo v Giovanni Oradini | 6-3,7-5 |
| Tunisia F15, Singles Qualifying | 2016/04/18 08:30 | Stefanini, Jacopo v Adrian Bodmer | 2-6,2-6 |
| Tunisia F15, Singles Qualifying | 2016/04/17 08:30 | Stefanini, Jacopo v Berg, Conor | 7-6,6-1 |
| Tunisia F14, Singles Qualifying | 2016/04/11 11:20 | Stefanini, Jacopo v Cunha-Silva, Felipe | 1-6,6-4,1-6 |
| ITF Morocco F3 | 2016/03/24 14:00 | Steven Diez v Stefanini, Jacopo | 6-2,6-0 |
| ITF Morocco F3 | 2016/03/20 10:00 | Stefanini, Jacopo v Chakrouni, Anas | 6-1,6-1 |
| ITF Italy F14 | 2016/06/07 07:30 | Di Nicola, Gianluca v Crepaldi, Erik | 6-1,7-5 |
| ITF Italy F12 | 2016/05/24 12:35 | Meis, Pascal v Di Nicola, Gianluca | 4-6,6-1,6-2 |
| ITF Italy F11 | 2016/05/22 08:45 | Capecchi, Daniele v Di Nicola, Gianluca | 7-5,3-6,2-6 |
| ITF Italy F11 | 2016/05/21 14:25 | Ghedin, Nicola v Di Nicola, Gianluca | 0-6,6-4,3-6 |
| ITF Italy F11 | 2016/05/20 15:00 | Di Nicola, Gianluca v Maden, Yannick | 0-6,6-4,6-2 |
| ITF Italy F11 | 2016/05/19 13:00 | Pancaldi, Luca v Di Nicola, Gianluca | 1-6,4-6 |
| ITF Italy F11 | 2016/05/18 08:30 | Di Nicola, Gianluca v Gian Marco Moroni | 4-6,6-2,6-3 |
| Italie F11, Qualifications Simples | 2016/05/16 14:35 | Di Nicola, Gianluca v Benjamin Pietri | 6-2,7-5 |