Round: 25 Ground: Clay
| ITF Italy F20 | 2016/07/12 10:00 | Antonio Massara v Andrea Guerrieri | 6-0,6-1 |
| 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 Serbia F3 | 2016/08/06 12:15 | Michael Linzer v Antonio Massara | 6-3,6-1 |
| ITF Italy F26 | 2016/08/24 11:00 | Hugo Grenier v Andrea Guerrieri | 6-4,6-2 |
| ITF Italy F26 | 2016/08/23 10:30 | Andrea Guerrieri v Jacopo Stefanini | 6-2,6-3 |
| ITF Italy F20 | 2016/07/12 10:00 | Antonio Massara v Andrea Guerrieri | 6-0,6-1 |
| ITF Italy F18 | 2016/06/27 18:45 | Andrea Guerrieri v Federico Maccari | 3-6,3-6 |
| ITF Italy F16 | 2016/06/21 14:00 | Francesco Picco v Andrea Guerrieri | 6-3,6-2 |
| ITF Italy F15 | 2016/06/15 11:30 | Markus Eriksson v Andrea Guerrieri | 6-2,6-3 |
| ITF Italy F15 | 2016/06/14 10:55 | Andrea Guerrieri v Filippo Baldi | 1-6,6-4,6-3 |
| ITF Croatia F1 | 2016/03/05 09:00 | Danilo Petrovic v Andrea Guerrieri | 6-1,7-6 |