Round: 27 Ground: Clay
| ITF Italy F27 | 2016/08/31 13:55 | Pol Toledo Bague v Tobias Simon | 3-6,4-6 |
| ITF Italy F27 | 2016/08/29 09:00 | Tobias Simon v Riccardo Roberto | 6-1,6-2 |
| 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 Italy F27 | 2016/08/31 17:00 | Luca Giacomini v Kristijan Mesaros | 3-6,4-6 |
| ITF Italy F27 | 2016/08/30 09:00 | Giovanni Oradini v Kristijan Mesaros | 4-6,3-6 |
| ITF Italy F25 | 2016/08/17 12:30 | Bastian Malla v Kristijan Mesaros | 6-2,6-0 |
| ITF Italy F25 | 2016/08/16 11:05 | David Vega Hernandez v Kristijan Mesaros | 2-6,4-6 |
| ITF Serbia F3 | 2016/08/07 08:30 | Michael Linzer v Kristijan Mesaros | 5-7,3-6 |
| ITF Serbia F3 | 2016/08/06 12:15 | Christopher O'Connell v Kristijan Mesaros | 3-6,3-6 |
| ITF Serbia F3 | 2016/08/04 09:25 | Alessandro Luisi v Kristijan Mesaros | 4-6,7-6,2-6 |
| ITF Serbia F3 | 2016/08/03 11:50 | Boris Butulija v Kristijan Mesaros | 1-6,1-6 |