Round: 25 Ground: Clay
| ITF Italy F21 Qual | 2016/07/16 10:30 | Federico Maccari v Marco Miceli | 4-6,6-7 |
| ITF Italy F18 | 2016/06/29 14:20 | Francesco Picco v Federico Maccari | 7-5,7-6 |
| ITF Italy F18 | 2016/06/27 18:45 | Andrea Guerrieri v Federico Maccari | 3-6,3-6 |
| ITF Italy F16 Qual | 2016/06/18 08:00 | Federico Maccari v Lorenzo Abbruciati | 3-6,5-7 |
| ITF Italy F15 | 2016/06/12 07:00 | Federico Maccari v Blake Ellis | 6-4,1-6,4-6 |
| ITF Italy F15 | 2016/06/11 07:30 | Federico Maccari v Daniele Chiurulli | 3-6,6-3,7-6 |
| ITF Italy F14 Qual | 2016/06/05 08:00 | Federico Maccari v Nicolo Turchetti | 3-6,6-2,3-6 |
| ITF Italy F13 | 2016/05/29 07:30 | Federico Maccari v Giovanni Oradini | 2-6,4-6 |
| 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 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 |