Round: 25 Ground: Clay
| Challenger Caltanissetta | 2016/06/07 18:35 | Marko Tepavac v Antonio Massara | 6-4,6-4 |
| Challenger Caltanissetta Qual | 2016/06/05 10:00 | Sergio Galdos v Antonio Massara | 3-6,3-6 |
| Challenger Caltanissetta Qual | 2016/06/04 13:05 | Antonio Massara v Riccardo Ghedin | 6-7,6-4,6-0 |
| Challenger Caltanissetta Qual | 2016/06/04 08:00 | Antonio Massara v Eduardo Dischinger | 6-4,6-2 |
| ITF Italy F13 | 2016/05/31 09:35 | Maverick Banes v Antonio Massara | 7-5,6-4 |
| ITF Italy F10 | 2016/05/10 07:30 | Mateo Nicolas Martinez v Antonio Massara | 6-3,6-2 |
| ITF Italy F9 | 2016/05/04 07:30 | Gian Marco Moroni v Antonio Massara | 7-5,6-2 |
| ITF Italy F9 | 2016/05/03 08:00 | Sergio Martos Gornes v Antonio Massara | 0-6,2-6 |
| ITF Poland F3 | 2016/06/07 11:25 | Michal Schmid v Patrik Niklas-Salminen | 7-6,2-6,2-6 |
| ITF Poland F2 | 2016/06/05 10:00 | Michal Schmid v Pawel Juszczak | 4-6,2-6 |
| ITF Poland F2 | 2016/06/03 09:20 | Sebastian Fanselow v Michal Schmid | 3-6,6-7 |
| ITF Poland F2 | 2016/06/02 08:00 | Adam Majchrowicz v Michal Schmid | 1-6,2-6 |
| ITF Israel F7 | 2016/05/19 09:55 | Michal Schmid v Edan Leshem | 4-6,2-6 |
| ITF Israel F7 | 2016/05/18 08:30 | Michal Schmid v Keivon Tabrizi | 6-4,6-1 |
| ITF Israel F7 | 2016/05/17 13:30 | Michal Schmid v Yannai Barkai | 6-2,7-5 |
| ITF Italy F7 | 2016/04/19 11:15 | Stefanos Tsitsipas v Michal Schmid | 7-6,7-6 |