Stadium: Centre Court Round: 24 Ground: Hardcourt indoor
| ITF Germany F13 | 2015/08/28 11:00 | Tobias Simon v Jeremy Jahn | 4-6,3-6 |
| ITF M25 Karlsruhe | 2019/06/05 13:40 | Jeremy Jahn v James Frawley | 6-2,3-6,7-6 |
| ITF M15 Quinta Do Lago | 2019/03/20 15:55 | Jonathan Binding v Jeremy Jahn | 2-6,1-6 |
| ITF M25 Kazan | 2019/03/14 08:35 | Jeremy Jahn v Ben Patael | 6-7,5-7 |
| ITF M25 Kazan | 2019/03/13 08:30 | Jeremy Jahn v Kristian Lozan | 6-1,6-3 |
| ITF M25 Kazan | 2019/03/13 07:00 | Jeremy Jahn v Kristian Lozan | 6-1,6-3 |
| ITF M25 Trento | 2019/03/03 09:30 | Jeremy Jahn v Jannik Sinner | 3-6,4-6 |
| ITF M25 Trento | 2019/03/02 13:00 | Julian Lenz v Jeremy Jahn | 6-7,3-6 |
| ITF M25 Trento | 2019/03/01 12:30 | Artem Dubrivnyy v Jeremy Jahn | 0-6,3-6 |
| ITF M25 Huelva | 2019/06/14 15:00 | Tobias Simon v Pol Martin Tiffon | 4-6,4-6 |
| ITF M25 Huelva | 2019/06/13 17:00 | Tobias Simon v Evan Furness | 6-3,6-7,6-1 |
| ITF M25 Huelva | 2019/06/12 13:25 | Tobias Simon v Luis Faria | 6-3,7-6 |
| Challenger Poznan | 2019/06/03 08:00 | Tobias Simon v Jacopo Berrettini | 2-6,4-6 |
| ITF M25 Most | 2019/05/29 08:00 | Tobias Simon v Dominik Recek | 5-7,4-6 |
| Challenger Samarkand | 2019/05/13 11:20 | Alexander Zhurbin v Tobias Simon | 7-6,6-7,7-5 |
| Challenger Shymkent | 2019/05/09 10:45 | Tobias Simon v Jay Clarke | 2-6,7-5,6-7 |
| Challenger Shymkent | 2019/05/07 08:10 | Viktor Durasovic v Tobias Simon | 6-7,5-7 |