Round: 26 Ground: Clay
| ITF Italy F20 | 2016/07/12 10:00 | Antonio Massara v Andrea Guerrieri | 6-0,6-1 |
| Challenger Todi | 2016/07/04 12:15 | Antonio Massara v Cem Ilkel | 6-3,5-7,5-7 |
| Challenger Todi | 2016/07/03 14:50 | Lucas Miedler v Antonio Massara | 6-4,6-7,3-6 |
| ITF Italy F18 | 2016/07/02 12:30 | Walter Trusendi v Antonio Massara | 6-1,6-1 |
| ITF Italy F18 | 2016/07/01 14:40 | Daniele Capecchi v Antonio Massara | 5-7,6-3,3-6 |
| ITF Italy F18 | 2016/06/29 12:30 | Simone Roncalli v Antonio Massara | 1-6,3-6 |
| ITF Italy F18 | 2016/06/28 10:10 | Giovanni Rizzuti v Antonio Massara | 4-6,3-6 |
| ITF Poland F4 | 2016/06/17 09:00 | Antonio Massara v Marcin Gawron | 4-6,0-6 |
| ITF Italy F20 | 2016/07/11 12:30 | Samuele Ramazzotti v Jacopo Stefanini | 3-6,6-4,4-6 |
| ITF Italy F18 Qual | 2016/06/25 10:00 | Jacopo Stefanini v Michele D'Amico | 6-1,6-4 |
| ITF Italy F16 | 2016/06/23 14:45 | Jacopo Stefanini v Hernan Casanova | 2-6,1-6 |
| ITF Italy F16 | 2016/06/22 12:10 | Gerard Granollers-Pujol v Jacopo Stefanini | 6-2,2-6,3-6 |
| ITF Italy F16 | 2016/06/21 10:55 | Andrea Bolla v Jacopo Stefanini | 6-4,4-6,4-6 |
| ITF Italy F15 | 2016/06/17 08:00 | Jacopo Stefanini v Walter Trusendi | 1-6,2-6 |
| ITF Italy F15 | 2016/06/16 12:25 | Tom Kocevar-Desman v Jacopo Stefanini | 3-6,6-7 |
| ITF Italy F15 | 2016/06/13 07:30 | Milos Sekulic v Jacopo Stefanini | 7-5,2-6,4-6 |