Round: 26 Ground: Clay
| ITF Austria F5 | 2015/07/21 10:30 | Simon, Tobias v Bogdan Bobrov | 6-2,6-3 |
| 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 Romania F5 | 2016/06/09 07:30 | Kekercheni, Filipp v Simon, Tobias | 3-6,6-3,1-6 |
| ITF Austria F4 | 2016/07/25 16:00 | Nareyka, Bjorn v Bogdan Bobrov | 3-6,3-6 |
| ITF Austria F4 Qual | 2016/07/24 08:00 | Bogdan Bobrov v Li, Yuanfeng | 6-3,0-6,6-4 |
| ITF Austria F4 Qual | 2016/07/23 12:00 | Bogdan Bobrov v Schranz, Bernie | 7-5,6-4 |
| ITF Austria F3 | 2016/07/21 08:00 | Ornago, Fabrizio v Bogdan Bobrov | 7-5,6-2 |
| ITF Austria F3 | 2016/07/20 09:30 | Bogdan Bobrov v Goncalo Oliveira | 1-6,6-4,6-3 |
| ITF Austria F3 | 2016/07/18 07:45 | Bogdan Bobrov v Florian Broska | 6-4,6-3 |
| ITF Austria F3 | 2016/07/17 09:00 | Bogdan Bobrov v Brna, David Damian | 5-7,6-4,6-4 |
| ITF Austria F3 | 2016/07/16 10:00 | Bogdan Bobrov v Nareyka, Bjorn | 6-2,4-6,6-4 |