Round: 27 Ground: Clay
| ITF Serbia F3 | 2016/08/04 08:00 | Antonio Massara v Manuel Pena Lopez | 6-3,6-1 |
| ITF Serbia F3 | 2016/08/03 11:05 | Antonio Massara v Davide Galoppini | 0-6,6-3,6-2 |
| 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 |
| ITF Serbia F3 | 2016/08/02 10:00 | Nicholas Horton v Filippo Leonardi | 6-2,2-6,6-3 |
| ITF Serbia F2 | 2016/07/28 08:00 | Nicholas Horton v Ljubomir Celebic | 4-6,3-6 |
| ITF Serbia F2 | 2016/07/27 08:00 | Nicholas Horton v Darko Jandric | 6-3,7-6 |
| ITF Serbia F2 Qual | 2016/07/24 08:00 | Nicholas Horton v Danylo Veremeychuk | 6-4,6-2 |
| ITF Serbia F1 | 2016/07/20 15:10 | Nerman Fatic v Nicholas Horton | 6-1,6-1 |
| ITF France F12 Qual | 2016/06/26 08:30 | Nicholas Horton v Juan Ignacio Iliev | 2-6,6-1,2-6 |
| ITF France F10 | 2016/06/16 12:00 | Nicholas Horton v Romain Arneodo | 2-6,1-6 |
| ITF France F10 | 2016/06/15 14:00 | Joffrey De Schepper v Nicholas Horton | 6-2,2-6,3-6 |