Stadium: Court 1 TC Avenue Round: 25 Ground: Clay
| ITF M15 Chornomorsk | 2019/09/24 07:00 | Vasko Mladenov v Gabriel Donev | 4-6,4-6 |
| ITF M15 Varna | 2019/09/10 06:30 | Vasko Mladenov v Ivan Mikhaylyuk | 6-3,6-3 |
| ITF M25 Irpin | 2019/08/26 07:30 | Vasko Mladenov v Danylo Veremeychuk | 4-6,4-6 |
| ITF M15 Minsk | 2019/08/21 09:25 | Vasko Mladenov v Ondrej Krstev | 4-6,4-6 |
| ITF M15 Irpin | 2019/08/13 11:50 | Sagadat Ayap v Vasko Mladenov | 7-5,6-4 |
| ITF M15 Plovdiv | 2019/06/06 09:10 | Dimitar Kuzmanov v Vasko Mladenov | 6-3,6-0 |
| 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 Chornomorsk | 2019/09/28 07:30 | Nikita Mashtakov v Vitaliy Sachko | 3-6,5-7 |
| ITF M15 Chornomorsk | 2019/09/27 12:15 | Oleksii Krutykh v Nikita Mashtakov | 5-7,2-6 |
| ITF M15 Chornomorsk | 2019/09/26 07:30 | Alexander Ovcharov v Nikita Mashtakov | 4-6,0-6 |
| ITF M15 Chornomorsk | 2019/09/25 11:15 | Aleksandr Braynin v Nikita Mashtakov | 3-6,7-5,3-6 |
| ITF M15 Targu Mures | 2019/09/20 08:45 | Bogdan Ionut Apostol v Nikita Mashtakov | 6-4,6-3 |
| ITF M15 Targu Mures | 2019/09/19 10:30 | Kuzey Cekirge v Nikita Mashtakov | 0-6,4-6 |
| ITF M15 Targu Mures | 2019/09/18 07:30 | Cezar Cretu v Nikita Mashtakov | 6-4,3-6,3-6 |
| ITF M15 Varna | 2019/09/13 11:15 | Juan Pablo Paz v Nikita Mashtakov | 6-2,6-3 |