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