Stadium: Court 6 Round: 25 Ground: Clay
| 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 Tabarka | 2019/04/11 08:45 | Vasko Mladenov v Filip Bergevi | 6-1,6-4 |
| Davis Cup | 2019/09/14 10:40 | Philip Henning v Gabriel Donev | 6-2,6-3 |
| ITF M15 Curtea de Arges | 2019/08/23 08:00 | Hernan Casanova v Gabriel Donev | 6-2,6-0 |
| ITF M15 Curtea de Arges | 2019/08/22 07:00 | Alexandru Vasile Manole v Gabriel Donev | 4-6,2-6 |
| ITF M25 Pitesti | 2019/08/14 06:00 | Gabriel Donev v Bogdan Pavel | 6-7,3-6 |
| ITF M15 Targu Mures | 2019/08/08 07:00 | Gabriel Donev v Facundo Juarez | 6-0,4-6,2-6 |
| ITF M15 Targu Mures | 2019/08/06 14:30 | Gabriel Donev v Doru Junior Borsan | 6-0,6-0 |
| ITF M15 Kramsach | 2019/07/17 13:30 | Gabriel Donev v Patrik Hartmeier | 4-6,3-6 |
| ITF M15 Telfs | 2019/07/10 11:25 | Sandro Ehrat v Gabriel Donev | 6-0,6-3 |