Round: 25 Ground: Clay
| ITF Germany F12 | 2016/08/26 13:00 | Torebko, Peter v Simon, Tobias | 7-5,7-5 |
| ITF Germany F12 | 2016/08/25 13:45 | Tom Schonenberg v Simon, Tobias | 6-7,2-6 |
| ITF Germany F12 | 2016/08/24 12:45 | Obert, Adrian v Simon, Tobias | 4-6,2-6 |
| ITF Switzerland F3 | 2016/08/20 09:00 | Laurent Lokoli v Simon, Tobias | 3-6,4-6 |
| ITF Switzerland F3 | 2016/08/19 10:00 | Simon, Tobias v Goncalo Oliveira | 7-5,4-6,6-3 |
| ITF Switzerland F3 | 2016/08/18 13:20 | Simon, Tobias v Maiga, Riccardo | 6-3,3-6,6-4 |
| ITF Switzerland F3 | 2016/08/17 09:30 | Simon, Tobias v Tashi, Vullnet | 6-1,1-6,6-1 |
| ITF Austria F5 | 2016/08/08 14:10 | Klegou, Alexis v Simon, Tobias | 2-6,2-6 |
| ITF Italy F27 | 2016/08/28 08:00 | Roberto, Riccardo v Mosciatti, Marco | 6-4,7-5 |
| ITF Italy F27 | 2016/08/27 11:00 | Moncagatto, Francesco v Roberto, Riccardo | 6-2,6-7,2-6 |
| ITF Italy F25 Qual | 2016/08/15 07:30 | Andres Gabriel Ciurletti v Roberto, Riccardo | 6-1,7-6 |
| ITF Italy F25 Qual | 2016/08/13 08:00 | Roberto, Riccardo v Ragazzi, Alessandro | 6-0,6-3 |
| ITF Italy F14 Qual | 2016/06/05 11:50 | Toby Martin v Roberto, Riccardo | 6-3,6-3 |
| ITF Italy F14 Qual | 2016/06/04 10:45 | Roberto, Riccardo v Jofre, Facundo | 7-5,6-2 |
| ITF Italy F13 | 2016/05/30 08:00 | Goncalo Oliveira v Roberto, Riccardo | 6-1,6-3 |
| ITF Italy F13 | 2016/05/29 07:30 | Russo, Cristiano v Roberto, Riccardo | 5-7,6-4,2-6 |