Stadium: Hard 3 Round: 26 Ground: Hardcourt outdoor
| ITF - M15 Heraklion | 2020/03/04 12:30 | Nicholas David Ionel v Vasil Kirkov | 5-7,3-6 |
| ITF - M15 Heraklion | 2020/02/29 11:20 | Vasil Kirkov v Nicholas David Ionel | 3-6,3-6 |
| ITF - M15 Heraklion | 2020/02/28 10:05 | Antonio Cayetano March v Vasil Kirkov | 1-6,3-6 |
| ITF - M15 Heraklion | 2020/02/27 08:30 | Vasil Kirkov v Lucas Catarina | 7-6,6-2 |
| ITF - M15 Heraklion | 2020/02/25 09:30 | Gabriele Maria Noce v Vasil Kirkov | 3-6,1-6 |
| Challenger - Drummondville | 2020/02/19 17:10 | Vasil Kirkov v Liam Broady | 6-3,3-6,4-6 |
| Challenger - Drummondville | 2020/02/18 15:00 | Lloyd Glasspool v Vasil Kirkov | 6-7,6-3,0-6 |
| Challenger - Cleveland | 2020/02/10 21:40 | Ulises Blanch v Vasil Kirkov | 6-2,6-3 |
| ITF - M15 Heraklion | 2020/03/04 09:15 | Nino Ehrenschneider v Matvey Khomentovskiy | 7-6,5-7,5-7 |
| ITF - M15 Heraklion | 2020/02/28 08:30 | Matvey Khomentovskiy v Kai Wehnelt | 6-7,6-3,0-6 |
| ITF - M15 Heraklion | 2020/02/27 08:30 | Ljubomir Celebic v Matvey Khomentovskiy | 3-6,6-3,3-6 |
| ITF - M15 Heraklion | 2020/02/26 08:30 | Matvey Khomentovskiy v Filip Bergevi | 7-6,6-1 |
| ITF - M15 Heraklion | 2020/02/16 11:00 | Matvey Khomentovskiy v Nicolas Tepmahc | 5-7,4-6 |
| ITF M15 - Kazan | 2020/01/22 11:15 | Mikhail Fufygin v Matvey Khomentovskiy | 6-2,6-3 |
| ITF M15 Prague | 2019/11/04 09:00 | Matvey Khomentovskiy v Daniel Siniakov | 1-6,2-6 |
| ITF M15 - Opava | 2019/10/30 12:05 | Petr Nouza v Matvey Khomentovskiy | 6-3,6-2 |