Round: 25 Ground: Clay
| ITF Italy F22 | 2016/07/26 17:00 | Jacopo Stefanini v Matteo Trevisan | 6-7,3-6 |
| ITF Italy F21 | 2016/07/19 12:00 | Federico Coria v Jacopo Stefanini | 6-2,6-2 |
| ITF Italy F21 Qual | 2016/07/17 09:30 | Jacopo Stefanini v Lorenzo Brunetti | 6-2,6-3 |
| ITF Italy F21 Qual | 2016/07/16 10:30 | Jacopo Stefanini v Andrea Bessire | 6-1,6-0 |
| ITF Italy F20 | 2016/07/15 12:30 | Jacopo Stefanini v Adelchi Virgili | 6-2,2-6,2-6 |
| ITF Italy F20 | 2016/07/13 12:00 | Antonio Massara v Jacopo Stefanini | 6-7,4-6 |
| ITF Italy F20 | 2016/07/11 12:30 | Samuele Ramazzotti v Jacopo Stefanini | 3-6,6-4,4-6 |
| ITF Italy F18 Qual | 2016/06/25 10:00 | Jacopo Stefanini v Michele D'Amico | 6-1,6-4 |
| ITF Italy F22 | 2016/07/29 19:30 | Andrea Basso v Marco Bortolotti | 6-2,7-6 |
| ITF Italy F22 | 2016/07/27 16:30 | Andres Gabriel Ciurletti v Marco Bortolotti | 3-6,2-6 |
| ITF Italy F22 | 2016/07/26 15:30 | Luca Tomasetto v Marco Bortolotti | 5-7,4-6 |
| ATP Bastad Qual | 2016/07/10 13:50 | Marco Bortolotti v Christian Lindell | 2-6,4-6 |
| Challenger Todi | 2016/07/04 16:45 | Salvatore Caruso v Marco Bortolotti | 6-3,4-6,6-1 |
| Challenger Todi | 2016/07/04 10:20 | Luca Margaroli v Marco Bortolotti | 1-6,6-7 |
| ITF Italy F16 | 2016/06/22 11:40 | Marco Bortolotti v Markus Eriksson | 5-7,2-6 |
| ITF Italy F16 | 2016/06/21 09:00 | Marco Bortolotti v Nicola Ghedin | 6-2,7-6 |