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 |
| UTR Pro Tennis Series California | 2020/07/19 21:10 | Bogdan Bobrov v Jurabek Karimov | 3-6,7-6,10-4 |
| UTR Pro Tennis Series California | 2020/07/18 18:15 | Toby D. Boyer v Bogdan Bobrov | 4-6,4-6 |
| UTR Pro Tennis Series California | 2020/07/17 21:10 | Martin Redlicki v Bogdan Bobrov | 6-4,6-4 |
| UTR Pro Tennis Series California | 2020/07/15 17:40 | Bogdan Bobrov v Christian Langmo | 1-6,4-6 |
| UTR Pro Tennis Series California | 2020/07/14 20:55 | Jurabek Karimov v Bogdan Bobrov | 2-6,6-7 |
| UTR Pro Tennis Series California | 2020/07/13 22:20 | Felix Corwin v Bogdan Bobrov | 6-4,6-0 |
| UTR Pro Tennis Series California | 2020/07/12 20:00 | Raymond Sarmiento v Bogdan Bobrov | 6-3,6-5 |
| UTR Pro Tennis Series California | 2020/07/12 18:50 | Raymond Sarmiento v Bogdan Bobrov | 6-3,7-5 |
| DTB German Pro Series | 2020/06/11 09:30 | Max Hans Rehberg v Tobias Simon | 3-6,7-6,6-3 |
| DTB German Pro Series | 2020/06/10 14:35 | Yannick Hanfmann v Tobias Simon | 6-3,6-2 |
| DTB German Pro Series | 2020/06/09 11:00 | Matthias Bachinger v Tobias Simon | 4-6,6-7 |
| Challenger Potchefstroom | 2020/03/11 09:30 | Adam Moundir v Tobias Simon | 5-7,3-6 |
| ITF M25 Potchefstroom | 2020/03/08 08:00 | Benjamin Bonzi v Tobias Simon | 7-6,6-4 |
| ITF M25 Potchefstroom | 2020/03/07 10:00 | Sadio Doumbia v Tobias Simon | 6-7,3-6 |
| ITF M25 Potchefstroom | 2020/03/06 08:00 | Corentin Denolly v Tobias Simon | 1-6,3-6 |
| ITF M25 Potchefstroom | 2020/03/05 11:50 | Tobias Simon v Daniel Masur | 6-3,3-6,6-3 |