Round: 27 Ground: Clay
| ITF Italy F31 | 2016/09/28 11:30 | Antonio Massara v Cristian Carli | 6-3,6-2 |
| ITF Italy F31 | 2016/09/26 09:00 | Antonio Massara v Andrea Guerrieri | 6-7,6-4,6-3 |
| ITF Italy F29 | 2016/09/14 08:25 | Jacopo Stefanini v Antonio Massara | 6-2,6-4 |
| ITF Italy F29 | 2016/09/13 09:25 | Simone Roncalli v Antonio Massara | 5-7,3-6 |
| Challenger Genova Qual | 2016/09/04 13:45 | Andrea Basso v Antonio Massara | 6-3,7-6 |
| Challenger Como Qual | 2016/08/27 14:30 | Antonio Massara v Markus Eriksson | 3-6,6-4,4-6 |
| ITF Italy F26 | 2016/08/24 17:00 | Matteo Trevisan v Antonio Massara | 4-6,6-3,6-3 |
| ITF Italy F26 | 2016/08/23 11:45 | Fran Zvonimir Zgombic v Antonio Massara | 4-6,1-6 |
| ITF Italy F31 | 2016/09/28 10:25 | Alex Rybakov v Maxime Chazal | 6-3,6-3 |
| ITF Italy F31 | 2016/09/28 01:41 | Alex Rybakov v Maxime Chazal | 6-3,6-3 |
| ITF Italy F31 | 2016/09/27 10:40 | Riccardo Sinicropi v Alex Rybakov | 6-7,1-6 |
| ITF Italy F30 | 2016/09/20 10:00 | Alex Rybakov v Stefano Travaglia | 2-6,7-6,2-6 |
| ITF Canada F7 | 2016/09/05 20:00 | David Volfson v Alex Rybakov | 6-7,6-2,6-2 |
| ITF USA F27 | 2016/08/09 17:20 | Takanyi Garanganga v Alex Rybakov | 6-4,6-4 |
| ITF USA F26 Qual | 2016/08/01 15:00 | Alex Rybakov v Alfredo Perez | 5-7,6-3,4-6 |
| ITF USA F17 | 2016/06/09 15:00 | Darian King v Alex Rybakov | 7-6,6-2 |