| UTR Pro Tennis Series - Sofia | 2021/08/30 07:00 | Leonid Sheyngezikht v Tadija Radovanovic | 6-2,6-3 |
| ITF - M15 Cairo | 2021/08/03 08:55 | Vladislav Ivanov v Leonid Sheyngezikht | 7-6,6-2 |
| ITF - M15 Cairo | 2021/08/03 07:30 | Vladislav Ivanov v Leonid Sheyngezikht | 7-6,6-2 |
| ITF - M15 Cairo | 2021/08/02 09:30 | Mohab Hamed v Leonid Sheyngezikht | 0-6,3-6 |
| ITF - M15 Cairo | 2021/08/01 12:30 | Ali Habib v Leonid Sheyngezikht | 4-6,3-6 |
| ITF - M15 Cairo | 2021/07/26 08:00 | Facundo Arias Bisso v Leonid Sheyngezikht | 7-5,6-1 |
| ITF - M15 Cairo | 2021/07/25 11:00 | Federico Luzzo v Leonid Sheyngezikht | 1-6,3-6 |
| ITF - M15 Cairo | 2021/07/22 08:00 | Kai Wehnelt v Leonid Sheyngezikht | 6-3,6-1 |
| UTR Pro Tennis Series - Sofia | 2021/08/30 10:00 | Alexandru Luca v Ivan Mikhaylyuk | 2-6,2-6 |
| ITF - M15 Sofia | 2021/07/05 13:30 | Ivan Mikhaylyuk v Andrew Fenty | 3-6,6-7 |
| ITF - M15 Sofia | 2021/07/05 08:00 | Christoffer Solberg v Ivan Mikhaylyuk | 1-6,3-6 |
| ITF - M15 Sofia | 2021/07/04 10:30 | Andrea Del Federico v Ivan Mikhaylyuk | 2-6,5-7 |
| ITF - M25 Belgrad | 2021/06/27 07:00 | Dusan Rajic v Ivan Mikhaylyuk | 2-6,6-0,12-10 |
| ITF - M15 Sharm El Sheikh | 2021/04/06 09:15 | Volodymyr Uzhylovskyi v Ivan Mikhaylyuk | 6-3,7-5 |
| ITF - M15 Sharm El Sheikh | 2021/04/04 07:30 | Bruno Stefani Figlio v Ivan Mikhaylyuk | 5-7,5-7 |
| ITF - M15 Sharm El Sheikh | 2021/03/29 11:30 | Issei Okamura v Ivan Mikhaylyuk | 6-1,6-2 |