Round: 27 Ground: Clay
| ITF Italy F24 | 2016/08/09 09:20 | Federico Gaio v Filippo Baldi | 6-4,2-6,7-6 |
| ITF Romania F10 | 2016/07/27 12:05 | Razvan Bobleaga v Filippo Baldi | 6-3,6-4 |
| ITF Italy F21 | 2016/07/19 11:00 | Filippo Baldi v Alberto Brizzi | 0-6,6-7 |
| ITF Italy F19 | 2016/07/06 08:00 | Filippo Baldi v Hernan Casanova | 3-6,1-6 |
| ITF Italy F19 | 2016/07/04 17:15 | Filippo Baldi v Alessandro Colella | 6-4,6-1 |
| ITF Italy F18 | 2016/06/30 14:00 | Daniele Capecchi v Filippo Baldi | 5-7,6-1,6-3 |
| Challenger Milan Qual | 2016/06/20 08:30 | Vaclav Safranek v Filippo Baldi | 6-4,7-5 |
| Challenger Milan Qual | 2016/06/19 12:00 | Filippo Baldi v Jose Hernandez-Fernandez | 7-5,6-4 |
| ITF Italy F25 Qual | 2016/08/13 08:00 | Riccardo Roberto v Alessandro Ragazzi | 6-0,6-3 |
| ITF Italy F14 Qual | 2016/06/05 11:50 | Toby Martin v Riccardo Roberto | 6-3,6-3 |
| ITF Italy F14 Qual | 2016/06/04 10:45 | Riccardo Roberto v Facundo Jofre | 7-5,6-2 |
| ITF Italy F13 | 2016/05/30 08:00 | Goncalo Oliveira v Riccardo Roberto | 6-1,6-3 |
| ITF Italy F13 | 2016/05/29 07:30 | Cristiano Russo v Riccardo Roberto | 5-7,6-4,2-6 |
| ITF Italy F13 | 2016/05/28 08:30 | Riccardo Roberto v Gil Uwe Grund | 6-2,7-6 |
| ITF Italy F11 Qual | 2016/05/16 14:55 | Cristian Carli v Riccardo Roberto | 6-2,6-3 |
| ITF Italy F11 Qual | 2016/05/16 10:10 | Riccardo Roberto v Augusto Virgili | 7-6,6-3 |