Round: 27 Ground: Clay
| 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 Austria F4 | 2016/07/28 09:00 | Tobias Simon v Goncalo Oliveira | 2-6,6-2,5-7 |
| ITF Austria F4 | 2016/07/27 13:10 | Tobias Simon v Bogdan Bobrov | 6-3,6-2 |
| ITF Austria F4 | 2016/07/26 14:10 | Tobias Simon v Farris Fathi Gosea | 6-2,6-3 |
| ITF Austria F2 | 2016/07/13 08:35 | Tobias Simon v Stefanos Tsitsipas | 6-4,2-6,2-6 |
| ITF Austria F2 | 2016/07/12 10:25 | Thales Turini v Tobias Simon | 4-6,3-6 |
| ITF Netherlands F3 | 2016/06/27 18:45 | Jelle Sels v Tobias Simon | 6-4,7-5 |
| ITF Switzerland F3 | 2016/08/17 09:30 | Riccardo Maiga v Marcos Giraldi Requena | 2-6,6-3,6-4 |
| ITF Switzerland F3 | 2016/08/15 09:00 | Andrew Ruppli v Riccardo Maiga | 3-6,0-6 |
| ITF Switzerland F3 Qual | 2016/08/14 08:00 | Loic Perret v Riccardo Maiga | 1-6,6-0,3-6 |
| ITF Switzerland F3 Qual | 2016/08/13 09:00 | Luca Giacomelli v Riccardo Maiga | 5-7,5-7 |
| ITF Latvia F1 | 2016/08/04 10:00 | Riccardo Maiga v Mikelis Libietis | 4-6,4-6 |
| ITF Latvia F1 | 2016/08/03 08:30 | Matvey Khomentovskiy v Riccardo Maiga | 5-7,0-6 |
| ITF Latvia F1 | 2016/08/02 10:05 | Fabian Gruber v Riccardo Maiga | 6-7,0-6 |
| ITF Latvia F1 | 2016/07/31 07:00 | Antoine Leduc v Riccardo Maiga | 0-6,0-6 |