Ground: Clay
| Challenger Meerbusch | 2019/08/13 08:00 | Thiemo De Bakker v Adam Pavlasek | 6-7,3-6 |
| Challenger Amersfoort | 2019/07/16 16:35 | Thiemo De Bakker v Jan Choinski | 2-6,7-5,2-6 |
| Challenger Braunschweig | 2019/07/07 10:10 | Lucas Miedler v Thiemo De Bakker | 6-4,7-6 |
| Challenger Ludwigshafen | 2019/07/03 14:55 | Thiemo De Bakker v Constant Lestienne | 3-6,4-6 |
| Challenger Ludwigshafen | 2019/07/02 09:00 | Sandro Ehrat v Thiemo De Bakker | 4-6,4-6 |
| Wimbledon | 2019/06/24 15:55 | Dennis Novak v Thiemo De Bakker | 6-4,6-3 |
| ATP Hertogenbosch | 2019/06/11 12:55 | Thiemo De Bakker v Adrian Mannarino | 2-6,1-6 |
| Challenger Prostejov | 2019/06/03 14:05 | Marcelo Arevalo v Thiemo De Bakker | 7-5,6-4 |
| Challenger Mallorca | 2019/08/28 12:35 | Peter Heller v Alejandro Davidovich Fokina | 5-7,4-6 |
| Challenger Mallorca | 2019/08/27 12:00 | Peter Heller v Inigo C Huegun | 6-4,1-6,7-5 |
| ITF M15 Ueberlingen | 2019/08/25 12:00 | Peter Heller v Louis Wessels | 6-1,6-4 |
| ITF M15 Ueberlingen | 2019/08/24 12:00 | Peter Heller v Bruno Santanna | 6-3,6-4 |
| ITF M15 Ueberlingen | 2019/08/23 10:00 | Peter Heller v Mick Veldheer | 6-3,7-6 |
| ITF M15 Ueberlingen | 2019/08/22 08:00 | Peter Heller v Valentin Guenther | 6-4,6-3 |
| ITF M15 Ueberlingen | 2019/08/21 09:55 | Peter Heller v Kai Lemstra | 5-7,6-2,6-2 |
| Challenger Augsburg | 2019/08/06 12:55 | Peter Heller v Mario Vilella Martinez | 2-6,2-6 |