Stadion: Court 3 TC Avenue Round: 26 Ground: Clay
| ITF - M15 - Burgas | 2019/10/09 12:55 | Simon A Ivanov v Vladimir Filip | 1-6,6-2,6-3 |
| ITF - M15 - Melilla | 2019/09/26 09:00 | Simon A Ivanov v Timofey Skatov | 3-6,2-6 |
| ITF - M15 - Melilla | 2019/09/24 11:30 | Jose Joaquin M Cisneros v Simon A Ivanov | 1-6,1-6 |
| ITF - M15 - Varna | 2019/09/13 08:55 | Juan Ignacio Galarza v Simon A Ivanov | 1-6,6-1,6-4 |
| ITF - M15 - Varna | 2019/09/12 09:20 | Luca Gelhardt v Simon A Ivanov | 3-6,1-6 |
| ITF - M15 - Varna | 2019/09/11 07:00 | Simon A Ivanov v Niklas Schell | 3-6,6-0,6-2 |
| ITF - M25 - Pozoblanco | 2019/08/08 17:40 | Simon A Ivanov v Konstantin Kravchuk | 3-6,6-7 |
| ITF - M25 - Pozoblanco | 2019/08/07 20:25 | Simon A Ivanov v Nicolas Alvarez Varona | 4-6,6-2,6-2 |
| 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 - Plovdiv | 2019/06/05 08:20 | Vasko Mladenov v Gorazd Srbljak | 3-6,6-4,6-4 |