Stadium: Court 1 Round: 44 Ground: Hardcourt outdoor
| UTR Pro Tennis Series Sofia | 2021/09/03 08:30 | Alexandar Lazarov v Leonid Sheyngezikht | 6-3,5-2 |
| UTR Pro Tennis Series Sofia | 2021/09/02 10:00 | Leonid Sheyngezikht v Viktor Markov | 6-2,5-3 |
| UTR Pro Tennis Series Sofia | 2021/09/01 09:30 | Leonid Sheyngezikht v Alexandru Luca | 6-3,6-2 |
| UTR Pro Tennis Series Sofia | 2021/08/31 06:30 | Leonid Sheyngezikht v Ivan Mikhaylyuk | 6-2,7-5 |
| 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 |
| Davis Kupa | 2021/06/25 09:00 | Connor H Van Schalkwyk v Frank Tayebwa | 6-0,6-0 |
| Davis Kupa | 2021/06/24 09:00 | Connor H Van Schalkwyk v Duhamel F Biboussy | 6-0,6-2 |
| Davis Kupa | 2021/06/23 09:00 | Connor H Van Schalkwyk v Fernando Andre | 6-2,6-1 |
| Davis Kupa | 2021/06/21 09:00 | Connor H Van Schalkwyk v Tshepo Mosarwa | 7-5,6-1 |