Round: 54 Ground: Hardcourt outdoor
| Challenger Ann Arbor | 2020/01/08 18:10 | Tobias Simon v Roberto Quiroz | 4-6,7-6,6-7 |
| Challenger Ann Arbor | 2020/01/06 22:25 | Tobias Simon v Evan King | 6-4,6-2 |
| ITF M15 - Heraklion | 2019/11/27 11:30 | Boris Pokotilov v Tobias Simon | 6-4,6-4 |
| ITF M15 - Sarreguemines | 2019/11/24 14:00 | Tobias Simon v Antoine Bellier | 4-6,6-7 |
| ITF M15 - Sarreguemines | 2019/11/23 15:40 | Hugo Schott v Tobias Simon | 6-7,6-7 |
| ITF M15 - Sarreguemines | 2019/11/22 15:35 | Tobias Simon v Jonathan Mridha | 6-7,6-4,6-4 |
| ITF M15 - Sarreguemines | 2019/11/21 13:35 | Tobias Simon v Justin Eleveld | 7-6,6-4 |
| ITF M15 - Sarreguemines | 2019/11/19 17:05 | Tobias Simon v Batiste Klein | 7-5,7-5 |
| ITF M25 - Claremont | 2019/10/07 18:00 | Jakob Schnaitter v Kyle Kang | 7-5,6-2 |
| ITF M25 - Claremont | 2019/10/06 18:00 | Kyle Overmyer v Kyle Kang | 7-6,3-6,5-10 |