Round: 1
| Davis Cup | 2020/03/08 00:50 | Jesse Flores v Dimitar Kuzmanov | 4-6,3-6 |
| Davis Cup | 2020/03/07 00:00 | Julian Saborio v Dimitar Kuzmanov | 4-6,2-6 |
| ITF - M25 Antalya | 2020/02/28 07:30 | Jonas Forejtek v Dimitar Kuzmanov | 6-4,3-6,7-5 |
| ITF - M25 Antalya | 2020/02/27 08:25 | Nikolas Sanchez Izquierdo v Dimitar Kuzmanov | 1-6,4-6 |
| ITF - M25 Antalya | 2020/02/26 12:25 | Marko Miladinovic v Dimitar Kuzmanov | 6-1,5-7,0-6 |
| Challenger - Koblenz | 2020/02/21 12:00 | Dimitar Kuzmanov v Tomas Machac | 4-6,4-6 |
| Challenger - Koblenz | 2020/02/20 14:00 | Dimitar Kuzmanov v Dustin Brown | 4-6,6-3,6-4 |
| Challenger - Koblenz | 2020/02/19 15:35 | Maxime Janvier v Dimitar Kuzmanov | 4-6,5-7 |
| ITF - M15 Heraklion | 2020/03/04 13:10 | Igor Saveljic v Hamad Medjedovic | 6-3,6-1 |
| ITF - M15 Heraklion | 2020/02/28 08:30 | Jordan Correia v Hamad Medjedovic | 6-2,6-1 |
| ITF - M15 Heraklion | 2020/02/27 10:35 | Hamad Medjedovic v Alexander Shevchenko | 6-0,7-5 |
| ITF - M15 Heraklion | 2020/02/26 08:30 | Jason Janis v Hamad Medjedovic | 0-6,2-6 |
| ITF M15 - Belgrado | 2019/07/04 08:00 | Hamad Medjedovic v Marko Miladinovic | 1-6,4-6 |
| ITF M15 - Belgrado | 2019/07/03 08:00 | Hamad Medjedovic v Gorazd Srbljak | 6-2,6-4 |