Stadium: Court 1 Round: 26 Ground: Clay
| ITF M15 Plovdiv | 2019/06/05 08:05 | Dimitar Kuzmanov v Nicolas Alberto Arreche | 6-3,6-3 |
| Challenger Jerusalem | 2019/05/23 08:40 | Dimitar Kuzmanov v Edan Leshem | 4-6,4-6 |
| Challenger Jerusalem | 2019/05/22 11:10 | Goncalo Oliveira v Dimitar Kuzmanov | 6-7,2-6 |
| Challenger Jerusalem | 2019/05/21 07:00 | Frederico Ferreira Silva v Dimitar Kuzmanov | 2-6,6-7 |
| ITF M15 Antalya | 2019/05/19 07:45 | Dimitar Kuzmanov v Oleg Prihodko | 3-6,6-2,6-1 |
| ITF M15 Antalya | 2019/05/18 09:50 | Dimitar Kuzmanov v Victor Vlad Cornea | 6-2,6-1 |
| ITF M15 Antalya | 2019/05/17 10:10 | Dimitar Kuzmanov v Marsel Ilhan | 6-2,6-3 |
| ITF M15 Antalya | 2019/05/16 09:15 | Dimitar Kuzmanov v Yanki Erel | 6-3,6-4 |
| ITF M15 Plovdiv | 2019/06/05 08:20 | Vasko Mladenov v Gorazd Srbljak | 3-6,6-4,6-4 |
| ITF M15 Tabarka | 2019/04/13 14:00 | Luigi Sorrentino v Vasko Mladenov | 1-6,6-4,6-3 |
| ITF M15 Tabarka | 2019/04/11 08:45 | Vasko Mladenov v Filip Bergevi | 6-1,6-4 |
| ITF M15 Tabarka | 2019/04/10 10:45 | Vasko Mladenov v Samuel Pointon | 6-2,3-6,6-0 |
| ITF M15 Tabarka | 2019/03/11 13:00 | Maxime Mora v Vasko Mladenov | 1-6,7-6,10-8 |
| ITF M15 Tabarka | 2019/03/11 08:00 | Gregorio Cordonnier v Vasko Mladenov | 4-6,5-7 |
| ITF M15 Tabarka | 2019/03/05 08:30 | Mikhail Korovin v Vasko Mladenov | 3-6,6-2,7-6 |
| ITF M15 Monastir | 2019/02/27 11:40 | Juan Pablo Paz v Vasko Mladenov | 6-3,3-6,6-3 |