Stadium: Court 1 Round: 54 Ground: Clay
| 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 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 Minsk | 2019/08/21 09:45 | Ivan Mikhaylyuk v David Volfson | 1-6,0-6 |
| ITF M15 Minsk | 2019/08/20 07:00 | Ivan Mikhaylyuk v Daniil Kakhniuk | 6-1,6-4 |
| ITF M15 Minsk | 2019/08/19 10:05 | Ivan Mikhaylyuk v Mohammad Khaled Abou Khamis | 6-0,6-0 |
| ITF M15 Telavi | 2019/07/29 08:00 | David Chelidze v Ivan Mikhaylyuk | 6-3,3-6,10-5 |
| ITF M15 Telavi | 2019/07/22 10:00 | Aliaksandr Liaonenka v Ivan Mikhaylyuk | 6-4,6-3 |
| ITF M15 Telavi | 2019/07/22 06:00 | Lukas H Lilleengen v Ivan Mikhaylyuk | 4-6,6-7 |
| ITF M15 Telavi | 2019/07/17 06:00 | Saida'lo Saidkarimov v Ivan Mikhaylyuk | 6-3,6-1 |
| ITF M15 Telavi | 2019/07/15 10:00 | Berk Ilkel v Ivan Mikhaylyuk | 2-6,1-6 |