Stadium: Center Court Round: 25 Ground: Hardcourt indoor
| Challenger Ortisei | 2018/10/07 08:00 | Christopher Heyman v Tobias Simon | 3-6,6-7 |
| 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 |
| Challenger Shymkent | 2019/05/06 05:40 | Tobias Simon v Gijs Brouwer | 3-6,6-4,7-5 |
| Challenger Bordeaux | 2019/04/29 08:00 | Tobias Simon v Hugo Nys | 2-6,4-6 |
| ITF M25 Angers | 2019/04/26 13:20 | Tobias Simon v Nikolas Sanchez Izquierdo | 6-2,5-7,2-6 |
| ITF M25 Angers | 2019/04/25 16:10 | Tobias Simon v Christoph Negritu | 6-4,6-7,6-0 |
| ITF M25 Angers | 2019/04/23 16:30 | Tobias Simon v Benjamin Dhoe | 6-3,4-6,6-4 |
| ITF M25 Sunderland | 2019/04/11 12:35 | Tobias Simon v Andres Artunedo Martinavarr | 2-6,0-6 |
| ITF M15 Antalya | 2019/04/27 07:30 | Jonas Forejtek v Christopher Heyman | 1-6,7-6,6-3 |
| ITF M15 Antalya | 2019/04/26 07:30 | Christopher Heyman v Yuta Shimizu | 7-6,6-4 |
| ITF M15 Antalya | 2019/04/25 10:40 | Christopher Heyman v Niklas Guttau | 7-6,7-5 |
| ITF M15 Antalya | 2019/04/24 07:00 | Christopher Heyman v Oleg Prihodko | 2-6,7-6,6-4 |
| ITF M15 Antalya | 2019/04/21 08:00 | Christopher Heyman v Christopher O'Connell | 4-6,6-3,7-6 |
| ITF M15 Antalya | 2019/04/20 07:30 | Alexander Shevchenko v Christopher Heyman | 7-5,2-6,5-7 |
| ITF M15 Antalya | 2019/04/19 07:30 | Christopher Heyman v Bogdan Bobrov | 6-7,6-3,6-3 |
| ITF M15 Antalya | 2019/04/18 09:00 | Christopher Heyman v Koray Kirci | 6-2,6-1 |