Round: 45 Ground: Clay
| ITF Italy F22 | 2016/07/30 16:00 | Antonio Massara v Andrea Basso | 6-7,6-3,4-6 |
| ITF Italy F27 | 2016/09/02 14:00 | Andrea Basso v Kristijan Mesaros | 2-6,2-6 |
| ITF Italy F27 | 2016/09/01 10:30 | Marco Bortolotti v Andrea Basso | 0-6,0-6 |
| ITF Italy F27 | 2016/08/31 13:40 | Andrea Basso v Matteo Viola | 6-4,7-6 |
| ITF Italy F27 | 2016/08/30 17:20 | Matteo Berrettini v Andrea Basso | 6-7,6-2,4-6 |
| ITF Italy F25 | 2016/08/16 07:30 | Andrea Basso v Nino Serdarusic | 6-2,7-5 |
| ITF Italy F22 | 2016/07/31 15:30 | Omar Giacalone v Andrea Basso | 5-7,3-6 |
| 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 19:30 | Andrea Basso v Marco Bortolotti | 6-2,7-6 |
| 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 Serbia F3 | 2016/08/05 09:20 | Antonio Massara v Nicholas Horton | 6-3,0-6,6-1 |
| 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 |