Round: 28 Ground: Clay
| ITF Italy F22 | 2016/07/29 14:30 | Moncagatto, Francesco v Antonio Massara | 5-7,5-7 |
| ITF Italy F22 | 2016/07/25 13:05 | Maccari, Federico v Antonio Massara | 2-6,3-6 |
| Challenger Recanati | 2016/07/20 13:00 | Dustov, Farrukh v Antonio Massara | 6-3,6-3 |
| ITF Italy F20 | 2016/07/13 12:00 | Antonio Massara v Stefanini, Jacopo | 6-7,4-6 |
| 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 | Trusendi, Walter v Antonio Massara | 6-1,6-1 |
| ITF Italy F22 | 2016/07/29 19:30 | Basso, Andrea v Bortolotti, Marco | 6-2,7-6 |
| ITF Italy F22 | 2016/07/27 11:20 | Roncalli, Simone v Basso, Andrea | 5-7,1-6 |
| ITF Italy F22 | 2016/07/25 09:30 | Fellin, Manfred v Basso, Andrea | 1-6,2-6 |
| ITF Italy F21 | 2016/07/21 13:30 | Federico Coria v Basso, Andrea | 3-6,6-4,7-5 |
| ITF Italy F21 | 2016/07/20 20:00 | Gabrieli, Tommaso v Basso, Andrea | 1-6,1-6 |
| ITF Italy F21 | 2016/07/19 13:35 | Basso, Andrea v Trusendi, Walter | 6-2,6-3 |
| Challenger San Benedetto | 2016/07/12 14:40 | Basso, Andrea v de Greef, Arthur | 6-4,4-6,4-6 |
| ITF Austria F1 | 2016/07/07 12:00 | Yannick Hanfmann v Basso, Andrea | 6-1,6-7,6-1 |