| ITF M15 Varna | 2019/09/10 06:30 | Vasko Mladenov v Ivan Mikhaylyuk | 6-3,6-3 |
| ITF M15 Burgas | 2019/10/10 10:10 | Simon A Ivanov v Vasko Mladenov | 3-6,6-2,6-2 |
| ITF M15 Burgas | 2019/10/09 09:00 | Vasko Mladenov v Nikita Mashtakov | 4-6,7-6,6-4 |
| 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 Sofia | 2021/07/05 13:30 | Ivan Mikhaylyuk v Andrew Fenty | 3-6,6-7 |
| ITF - M15 Sofia | 2021/07/05 08:00 | Christoffer Solberg v Ivan Mikhaylyuk | 1-6,3-6 |
| ITF - M15 Sofia | 2021/07/04 10:30 | Andrea Del Federico v Ivan Mikhaylyuk | 2-6,5-7 |
| ITF - M25 Belgrad | 2021/06/27 07:00 | Dusan Rajic v Ivan Mikhaylyuk | 2-6,6-0,12-10 |
| ITF - M15 Sharm El Sheikh | 2021/04/06 09:15 | Volodymyr Uzhylovskyi v Ivan Mikhaylyuk | 6-3,7-5 |
| ITF - M15 Sharm El Sheikh | 2021/04/04 07:30 | Bruno Stefani Figlio v Ivan Mikhaylyuk | 5-7,5-7 |
| ITF - M15 Sharm El Sheikh | 2021/03/29 11:30 | Issei Okamura v Ivan Mikhaylyuk | 6-1,6-2 |
| ITF - M15 Sharm El Sheikh | 2021/03/28 14:30 | Ivan Mikhaylyuk v Christian Sigsgaard | 4-6,6-4,10-2 |