Round: 26 Ground: Clay
| ITF Italy F20 | 2016/07/13 12:00 | Antonio Massara v Jacopo Stefanini | 6-7,4-6 |
| ITF Italy F28 | 2016/09/07 09:00 | Jacopo Stefanini v Omar Giacalone | 2-6,6-1,0-6 |
| ITF Italy F27 | 2016/08/31 11:25 | Jacopo Stefanini v Attila Balazs | 7-5,0-6,4-6 |
| ITF Italy F27 | 2016/08/30 12:50 | Nik Razborsek v Jacopo Stefanini | 6-7,7-6,1-6 |
| ITF Italy F26 | 2016/08/23 10:30 | Andrea Guerrieri v Jacopo Stefanini | 6-2,6-3 |
| ITF Italy F23 | 2016/08/06 08:00 | Jose Hernandez-Fernandez v Jacopo Stefanini | 6-3,6-4 |
| ITF Italy F23 | 2016/08/04 12:30 | Wilson Leite v Jacopo Stefanini | 3-6,2-6 |
| ITF Italy F23 | 2016/08/03 08:30 | Cristian Carli v Jacopo Stefanini | 6-7,2-6 |
| ITF Italy F23 | 2016/08/01 15:05 | Jacopo Stefanini v Marco Bortolotti | 4-6,7-6,7-6 |
| ITF Italy F29 | 2016/09/13 09:25 | Simone Roncalli v Antonio Massara | 5-7,3-6 |
| Challenger Genova Qual | 2016/09/04 13:45 | Andrea Basso v Antonio Massara | 6-3,7-6 |
| Challenger Como Qual | 2016/08/27 14:30 | Antonio Massara v Markus Eriksson | 3-6,6-4,4-6 |
| ITF Italy F26 | 2016/08/24 17:00 | Matteo Trevisan v Antonio Massara | 4-6,6-3,6-3 |
| ITF Italy F26 | 2016/08/23 11:45 | Fran Zvonimir Zgombic v Antonio Massara | 4-6,1-6 |
| ITF Serbia F4 | 2016/08/09 09:10 | Milan Drinic v Antonio Massara | 1-6,6-3,7-6 |
| ITF Serbia F3 | 2016/08/06 12:15 | Michael Linzer v Antonio Massara | 6-3,6-1 |
| ITF Serbia F3 | 2016/08/05 09:20 | Antonio Massara v Nicholas Horton | 6-3,0-6,6-1 |