Round: 27 Ground: Clay
| ITF Serbia F3 | 2016/08/04 08:00 | Antonio Massara v Pena Lopez, Manuel | 6-3,6-1 |
| ITF Serbia F3 | 2016/08/03 11:05 | Antonio Massara v Galoppini, Davide | 0-6,6-3,6-2 |
| ITF Italy F22 | 2016/07/30 16:00 | Antonio Massara v Basso, Andrea | 6-7,6-3,4-6 |
| 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 |
| ITF Serbia F3 | 2016/08/02 10:00 | Horton, Nicholas v Leonardi, Filippo | 6-2,2-6,6-3 |
| ITF Serbia F2 | 2016/07/28 08:00 | Horton, Nicholas v Celebic, Ljubomir | 4-6,3-6 |
| ITF Serbia F2 | 2016/07/27 08:00 | Horton, Nicholas v Jandric, Darko | 6-3,7-6 |
| ITF Serbia F2 Qual | 2016/07/24 08:00 | Horton, Nicholas v Veremeychuk, Danylo | 6-4,6-2 |
| ITF Serbia F1 | 2016/07/20 15:10 | Nerman Fatic v Horton, Nicholas | 6-1,6-1 |
| ITF France F12 Qual | 2016/06/26 08:30 | Horton, Nicholas v Iliev, Juan Ignacio | 2-6,6-1,2-6 |
| ITF France F10 | 2016/06/16 12:00 | Horton, Nicholas v Arneodo, Romain | 2-6,1-6 |
| ITF France F10 | 2016/06/15 14:00 | Joffrey De Schepper v Horton, Nicholas | 6-2,2-6,3-6 |