Stadium: Clay 3 Round: 26 Ground: Clay
| ITF M15 Antalya | 2019/09/24 07:00 | Guy Den Heijer v Alejandro H Franco | 7-6,6-0 |
| ITF M15 Haren | 2019/08/29 13:10 | Guy Den Heijer v Ryan Nijboer | 3-6,3-6 |
| ITF M15 Haren | 2019/08/28 10:20 | Alec Adamson v Guy Den Heijer | 2-6,2-6 |
| ITF M15 Oldenzaal | 2019/08/15 15:20 | Zachary Eisinga v Guy Den Heijer | 7-6,7-5 |
| ITF M15 Oldenzaal | 2019/08/14 17:20 | Jannik Rother v Guy Den Heijer | 7-5,3-6,4-6 |
| ITF M15 Eupen | 2019/08/07 08:00 | Guy Den Heijer v Daniel De Jonge | 2-6,3-6 |
| 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 | Guy Den Heijer v Jesper De Jong | 6-4,4-6,6-0 |
| ITF M15 Antalya | 2019/09/25 07:30 | Luca Gelhardt v Dimitar Kuzmanov | 1-6,2-6 |
| Davis Kupa | 2019/09/14 08:25 | Lloyd Harris v Dimitar Kuzmanov | 6-3,7-6 |
| Davis Kupa | 2019/09/13 12:05 | Ruan Roelofse v Dimitar Kuzmanov | 5-7,5-7 |
| Challenger Tampere | 2019/07/22 12:30 | Dimitar Kuzmanov v Andrea Pellegrino | 4-6,6-3,7-5 |
| Challenger Amersfoort | 2019/07/16 14:25 | Dimitar Kuzmanov v Kimmer Coppejans | 3-6,6-1,1-6 |
| Challenger Amersfoort | 2019/07/15 08:00 | Geoffrey Blancaneaux v Dimitar Kuzmanov | 5-7,1-6 |
| ITF M25 Cuneo | 2019/07/05 10:30 | Gijs Brouwer v Dimitar Kuzmanov | 6-7,6-4,6-2 |
| ITF M25 Cuneo | 2019/07/04 09:30 | Remy Bertola v Dimitar Kuzmanov | 2-6,0-6 |