Round: 27 Ground: Clay
| 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 Netherlands F1 | 2016/06/14 10:55 | Veldheer, Mick v Simon, Tobias | 1-6,2-6 |
| ITF Romania F5 | 2016/06/11 10:00 | Marcora, Roberto v Simon, Tobias | 6-7,6-1,7-6 |
| ITF Romania F5 | 2016/06/10 09:00 | Turini, Thales v Simon, Tobias | 1-6,3-6 |
| ITF Austria F4 | 2016/07/27 10:00 | David Pichler v Goncalo Oliveira | 3-6,5-7 |
| ITF Austria F4 | 2016/07/26 15:30 | Toby Martin v Goncalo Oliveira | 1-6,4-6 |
| ITF Austria F3 | 2016/07/20 09:30 | Bogdan Bobrov v Goncalo Oliveira | 1-6,6-4,6-3 |
| ITF Austria F2 | 2016/07/13 09:40 | Goncalo Oliveira v Schroll, Philipp | 6-3,1-6,6-3 |
| ITF Austria F2 | 2016/07/12 11:10 | Goncalo Oliveira v Aichhorn, Jakob | 6-2,6-1 |
| ITF Austria F1 | 2016/07/09 09:00 | Yannick Hanfmann v Goncalo Oliveira | 6-7,6-3,1-6 |
| ITF Austria F1 | 2016/07/08 10:00 | Goncalo Oliveira v Meis, Pascal | 6-4,6-0 |
| ITF Austria F1 | 2016/07/07 10:30 | Kapas, Andriej v Goncalo Oliveira | 2-6,0-6 |