Round: 25 Ground: Clay
| ITF Germany F12 | 2016/08/26 13:00 | Peter Torebko v Tobias Simon | 7-5,7-5 |
| ITF Germany F12 | 2016/08/25 13:45 | Tom Schonenberg v Tobias Simon | 6-7,2-6 |
| ITF Germany F12 | 2016/08/24 12:45 | Adrian Obert v Tobias Simon | 4-6,2-6 |
| ITF Switzerland F3 | 2016/08/20 09:00 | Laurent Lokoli v Tobias Simon | 3-6,4-6 |
| ITF Switzerland F3 | 2016/08/19 10:00 | Tobias Simon v Goncalo Oliveira | 7-5,4-6,6-3 |
| ITF Switzerland F3 | 2016/08/18 13:20 | Tobias Simon v Riccardo Maiga | 6-3,3-6,6-4 |
| ITF Switzerland F3 | 2016/08/17 09:30 | Tobias Simon v Vullnet Tashi | 6-1,1-6,6-1 |
| ITF Austria F5 | 2016/08/08 14:10 | Alexis Klegou v Tobias Simon | 2-6,2-6 |
| ITF Italy F27 | 2016/08/28 08:00 | Riccardo Roberto v Marco Mosciatti | 6-4,7-5 |
| ITF Italy F27 | 2016/08/27 11:00 | Francesco Moncagatto v Riccardo Roberto | 6-2,6-7,2-6 |
| ITF Italy F25 Qual | 2016/08/15 07:30 | Andres Gabriel Ciurletti v Riccardo Roberto | 6-1,7-6 |
| 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 |