Round: 25 Ground: Clay
| ITF Italy F20 Qual | 2015/07/26 10:00 | Antonio Massara v Davide Galoppini | 6-4,6-2 |
| ITF Italy F37 | 2014/10/19 07:30 | Antonio Massara v Davide Galoppini | 5-7,2-6 |
| ITF Italy F22 | 2016/07/30 16:00 | Antonio Massara v Andrea Basso | 6-7,6-3,4-6 |
| ITF Italy F22 | 2016/07/29 14:30 | Francesco Moncagatto v Antonio Massara | 5-7,5-7 |
| ITF Italy F22 | 2016/07/25 13:05 | Federico Maccari v Antonio Massara | 2-6,3-6 |
| Challenger Recanati | 2016/07/20 13:00 | Farrukh Dustov v Antonio Massara | 6-3,6-3 |
| ITF Italy F20 | 2016/07/13 12:00 | Antonio Massara v Jacopo Stefanini | 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 F22 | 2016/07/30 19:20 | Davide Galoppini v Omar Giacalone | 4-6,3-6 |
| ITF Italy F22 | 2016/07/29 17:00 | Davide Galoppini v Daniele Capecchi | 6-4,6-2 |
| ITF Italy F22 | 2016/07/28 17:00 | Davide Galoppini v Matteo Trevisan | 4-6,6-0,7-6 |
| ITF Italy F22 | 2016/07/26 11:15 | Julien Cagnina v Davide Galoppini | 4-6,2-6 |
| ITF Italy F20 | 2016/07/17 15:30 | Davide Galoppini v Andrea Pellegrino | 4-6,6-1,4-6 |
| ITF Italy F20 | 2016/07/16 15:00 | Davide Galoppini v Adelchi Virgili | 6-2,6-1 |
| ITF Italy F20 | 2016/07/15 12:30 | Davide Galoppini v Riccardo Balzerani | 6-3,4-6,6-3 |
| ITF Italy F20 | 2016/07/13 14:35 | Juan Pablo Paz v Davide Galoppini | 3-6,4-6 |