Stadium: Center Court Round: 25 Ground: Hardcourt indoor
| Challenger Ortisei | 2018/10/07 08:00 | Christopher Heyman v Tobias Simon | 3-6,6-7 |
| ITF M25 Schlieren | 2019/08/22 11:25 | Benjamin Bonzi v Tobias Simon | 6-2,6-3 |
| ITF M25 Schlieren | 2019/08/21 09:55 | Tobias Simon v Patrik Hartmeier | 6-3,6-3 |
| Challenger Portoroz | 2019/08/14 14:40 | Zdenek Kolar v Tobias Simon | 6-2,6-4 |
| Challenger Portoroz | 2019/08/12 15:30 | Quentin Robert v Tobias Simon | 3-6,5-7 |
| ITF M25 Pozoblanco | 2019/08/08 17:30 | Tobias Simon v Rayane Roumane | 6-3,3-6,6-7 |
| ITF M25 Pozoblanco | 2019/08/07 17:15 | Tobias Simon v Juan P Canas Garcia | 7-5,6-2 |
| Challenger Segovia | 2019/08/01 14:05 | Constant Lestienne v Tobias Simon | 7-6,6-2 |
| Challenger Segovia | 2019/07/30 08:00 | Tobias Simon v Aldin Setkic | 7-5,6-4 |
| Challenger Meerbusch | 2019/08/12 12:35 | Jelle Sels v Christopher Heyman | 6-2,3-6,6-1 |
| ITF M15 Brussels | 2019/08/04 12:00 | Christopher Heyman v Guy Den Heijer | 2-6,6-0,6-4 |
| ITF M15 Brussels | 2019/08/03 11:00 | Christopher Heyman v Nick Hardt | 6-2,6-3 |
| ITF M15 Brussels | 2019/08/02 13:15 | Christopher Heyman v Dominik Boehler | 7-6,6-4 |
| ITF M15 Brussels | 2019/08/01 12:45 | Christopher Heyman v Tuur Heuvinck | 6-2,6-2 |
| ITF M15 Brussels | 2019/07/30 13:15 | Christopher Heyman v Matvey Minin | 6-4,6-1 |
| Challenger Tampere | 2019/07/23 07:00 | Alexander Zhurbin v Christopher Heyman | 6-4,6-2 |
| Challenger Amersfoort | 2019/07/16 11:30 | Christopher Heyman v Mohamed Safwat | 2-6,1-6 |