Stadium: Center Court Round: 26 Ground: Carpet indoor
| DTB German Pro Series | 2020/06/09 11:00 | Matthias Bachinger v Tobias Simon | 4-6,6-7 |
| Challenger Prague | 2020/08/15 10:30 | Matthias Bachinger v Petr Nouza | 3-6,6-4,3-6 |
| DTB German Pro Series | 2020/06/26 09:45 | Peter Heller v Matthias Bachinger | 6-3,3-6,2-6 |
| DTB German Pro Series | 2020/06/25 08:00 | Matthias Bachinger v Philip Florig | 6-3,6-2 |
| DTB German Pro Series | 2020/06/24 08:00 | Matthias Bachinger v Peter Heller | 6-7,4-6 |
| DTB German Pro Series | 2020/06/23 08:00 | Matthias Bachinger v Niklas Guttau | 6-3,6-1 |
| DTB German Pro Series | 2020/06/11 13:25 | Yannick Hanfmann v Matthias Bachinger | 6-4,6-4 |
| DTB German Pro Series | 2020/06/10 09:45 | Matthias Bachinger v Max Hans Rehberg | 2-6,4-6 |
| DTB German Pro Series | 2020/06/09 11:00 | Matthias Bachinger v Tobias Simon | 4-6,6-7 |
| 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 |
| 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 |