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 Novomoskovsk | 2020/09/06 08:00 | Bogdan Bobrov v Oleksii Krutykh | 6-3,6-3 |
| ITF M15 Novomoskovsk | 2020/09/05 07:00 | Yaraslav Shyla v Bogdan Bobrov | 6-0,1-6,4-6 |
| ITF M15 Novomoskovsk | 2020/09/04 07:00 | Bogdan Bobrov v Ivan Sergeyev | 5-7,6-2,6-4 |
| ITF M15 Novomoskovsk | 2020/09/03 08:35 | Bogdan Bobrov v George Loffhagen | 6-3,6-3 |
| ITF M15 Novomoskovsk | 2020/09/01 07:00 | Bogdan Bobrov v Alex Barrena | 6-1,6-2 |
| UTR Pro Tennis Series California | 2020/08/11 17:30 | Dusty H. Boyer v Bogdan Bobrov | 3-6,1-6 |
| UTR Pro Tennis Series California | 2020/08/11 16:00 | Gage Brymer v Bogdan Bobrov | 6-3,6-3 |
| UTR Pro Tennis Series California | 2020/08/10 16:00 | Shahin Khaledan v Bogdan Bobrov | 1-6,7-5,4-10 |
| ITF M25 Plaisir | 2020/09/15 17:35 | Mathys Erhard v Tobias Simon | 6-7,4-6 |
| ITF M15 Caslano | 2020/09/01 13:20 | Sandro Ehrat v Tobias Simon | 6-4,6-4 |
| ITF M15 Anif | 2020/08/26 13:20 | Tobias Simon v Alexander Shevchenko | 3-6,1-6 |
| ITF M25 Vogau | 2020/08/20 12:55 | Tobias Simon v Igor Sijsling | 5-7,4-6 |
| ITF M25 Vogau | 2020/08/19 08:00 | Francisco Cerundolo v Tobias Simon | 3-6,6-7 |
| German Premier League | 2020/07/29 14:55 | Philipp Kohlschreiber v Tobias Simon | 6-4,6-2 |
| German Premier League | 2020/07/28 11:50 | Tobias Simon v Luc Fomba | 7-6,6-2 |
| German Premier League | 2020/07/27 13:00 | Tobias Simon v Alexey Vatutin | 6-7,6-3,2-6 |