Round: 26 Ground: Clay
| 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 Serbia F4 | 2016/08/09 09:10 | Milan Drinic v Antonio Massara | 1-6,6-3,7-6 |
| ITF Italy F31 | 2016/09/27 07:30 | Cristian Carli v Delf Gohlke | 6-1,6-2 |
| ITF Italy F30 | 2016/09/19 07:00 | Cristian Carli v Filippo Leonardi | 6-7,6-3,1-6 |
| ITF Italy F29 | 2016/09/14 08:30 | Gabriel Alejandro Hidalgo v Cristian Carli | 6-3,6-4 |
| ITF Italy F29 | 2016/09/12 07:30 | Cristian Carli v Samuel Bensoussan | 6-0,7-5 |
| ITF Italy F29 | 2016/09/11 07:30 | Cristian Carli v Jacopo Berrettini | 7-5,7-6 |
| ITF Italy F28 | 2016/09/06 10:30 | Cristian Carli v Andrea Pellegrino | 3-6,6-7 |
| ITF Italy F28 | 2016/09/05 10:00 | Cristian Carli v Giovanni Oradini | 4-6,6-2,7-6 |
| ITF Italy F28 | 2016/09/04 12:30 | Cristian Carli v Lorenzo Di Maro | 6-0,6-2 |