Estádio: Court 1 Round: 27 Ground: Clay
| ITF - M15 Plovdiv | 2019/06/06 09:10 | Dimitar Kuzmanov v Vasko Mladenov | 6-3,6-0 |
| ITF - M15 Plovdiv | 2019/06/05 08:05 | Dimitar Kuzmanov v Nicolas Alberto Arreche | 6-3,6-3 |
| Challenger - Jerusalém | 2019/05/23 08:40 | Dimitar Kuzmanov v Edan Leshem | 4-6,4-6 |
| Challenger - Jerusalém | 2019/05/22 11:10 | Goncalo Oliveira v Dimitar Kuzmanov | 6-7,2-6 |
| Challenger - Jerusalém | 2019/05/21 07:00 | Frederico Ferreira Silva v Dimitar Kuzmanov | 2-6,6-7 |
| ITF - M15 Antália | 2019/05/19 07:45 | Dimitar Kuzmanov v Oleg Prihodko | 3-6,6-2,6-1 |
| ITF - M15 Antália | 2019/05/18 09:50 | Dimitar Kuzmanov v Victor Vlad Cornea | 6-2,6-1 |
| ITF - M15 Antália | 2019/05/17 10:10 | Dimitar Kuzmanov v Marsel Ilhan | 6-2,6-3 |
| ITF - M15 Plovdiv | 2019/06/06 07:00 | Dan Alexandru Tomescu v Vladyslav Orlov | 1-6,6-7 |
| ITF - M15 Plovdiv | 2019/06/04 11:00 | Vladyslav Orlov v Nicolae Frunza | 7-6,6-3 |
| ITF - M25 Gyula | 2019/05/29 07:00 | Vladyslav Orlov v Matej Sabanov | 6-4,2-6,3-6 |
| ITF - M15 Irpin | 2019/05/25 08:00 | Artem Smirnov v Vladyslav Orlov | 6-2,6-3 |
| ITF - M15 Irpin | 2019/05/24 08:00 | Vladyslav Orlov v Oleg Dolgosheyev | 6-1,6-1 |
| ITF - M15 Irpin | 2019/05/23 08:00 | Nikita Mashtakov v Vladyslav Orlov | 4-6,2-6 |
| ITF - M15 Irpin | 2019/05/22 08:40 | Vladyslav Orlov v Jordan Correia | 0-6,6-4,6-4 |
| ITF - M15 Irpin | 2019/05/21 07:00 | Vladyslav Orlov v Vitalii Shcherba | 6-4,3-6,7-6 |