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