Stadium: Court 3 Round: 27 Ground: Clay
| ITF M15 Doha | 2019/10/20 13:00 | Tobias Simon v Bogdan Bobrov | 6-3,7-5 |
| ITF Austria F4 | 2016/07/27 13:10 | Tobias Simon v Bogdan Bobrov | 6-3,6-2 |
| ITF Austria F5 | 2015/07/21 10:30 | Tobias Simon v Bogdan Bobrov | 6-2,6-3 |
| ITF M15 Bratislava | 2020/11/26 08:55 | Bogdan Bobrov v Alexis Canter | 0-6,7-5,7-5 |
| ITF M15 Bratislava | 2020/11/25 10:40 | Bogdan Bobrov v Michal Novansky | 3-6,6-4,7-6 |
| ITF M15 Sharm El Sheikh | 2020/11/18 09:40 | Bogdan Bobrov v Siddhant Banthia | 6-4,6-7,3-6 |
| ITF M15 Sharm El Sheikh | 2020/11/14 08:00 | Bogdan Bobrov v Petros Chrysochos | 3-6,3-6 |
| ITF M15 Sharm El Sheikh | 2020/11/13 08:00 | Christian Langmo v Bogdan Bobrov | 2-6,5-7 |
| ITF M15 Sharm El Sheikh | 2020/11/12 10:55 | Jeffrey Von Der Schulenburg v Bogdan Bobrov | 3-6,3-6 |
| ITF M15 Sharm El Sheikh | 2020/11/11 12:10 | Gauthier Onclin v Bogdan Bobrov | 5-7,6-4,5-7 |
| ITF M15 Sharm El Sheikh | 2020/11/05 10:20 | Bogdan Bobrov v Yaraslav Shyla | 7-5,3-6,2-6 |
| ITF M15 Bratislava | 2020/11/26 13:25 | Tomas Jirousek v Tobias Simon | 1-6,5-7 |
| ITF M15 Bratislava | 2020/11/25 13:45 | Yann Marti v Tobias Simon | 3-6,6-7 |
| Challenger Bratislava | 2020/11/07 17:30 | Mathias Bourgue v Tobias Simon | 6-4,6-2 |
| Challenger Eckental | 2020/10/31 10:30 | Matthias Bachinger v Tobias Simon | 7-6,6-4 |
| ITF M15 Sarreguemines | 2020/10/29 09:25 | Tobias Simon v Maxence Broville | 6-3,7-6 |
| ITF M15 Sarreguemines | 2020/10/27 16:30 | Tobias Simon v Alexis Gautier | 6-3,6-4 |
| ITF M15 Setubal | 2020/10/06 09:00 | Evan Furness v Tobias Simon | 6-3,7-5 |
| ITF M15 Forbach | 2020/10/01 11:55 | Johan Sebastien Tatlot v Tobias Simon | 6-3,6-3 |