Stadium: Court 5 Round: 25 Ground: Clay
| ITF Bahrain F1 | 2015/03/23 08:00 | Peter Heller v Tobias Simon | 7-5,6-7,3-6 |
| 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 |
| 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 |
| Challenger Heilbronn | 2019/05/15 09:30 | Matthias Bachinger v Peter Heller | 6-3,6-3 |
| Challenger Heilbronn | 2019/05/14 09:30 | Peter Heller v Kevin Krawietz | 6-3,6-2 |
| Challenger Rome | 2019/05/07 12:40 | Peter Heller v Henri Laaksonen | 2-6,1-6 |
| Challenger Rome | 2019/05/06 10:10 | Peter Heller v Gregoire Jacq | 6-3,6-3 |
| Challenger Ostrava | 2019/05/01 12:50 | Norbert Gombos v Peter Heller | 6-4,7-5 |
| Challenger Ostrava | 2019/04/29 14:10 | Emil Ruusuvuori v Peter Heller | 6-7,4-6 |
| Challenger Barletta | 2019/04/09 11:30 | Sumit Nagal v Peter Heller | 1-6,6-1,6-0 |
| Challenger Sophia Antipolis | 2019/04/02 09:50 | Peter Heller v Simone Bolelli | 2-6,5-7 |