Stadium: Court 1 Round: 44 Ground: Hardcourt outdoor
| ITF M25 Johannesburg | 2021/09/13 07:25 | Leonid Sheyngezikht v Neil Oberleitner | 6-3,1-6,10-4 |
| 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 M25 Johannesburg | 2021/09/13 07:30 | Anro Nel v Muzi Sibanda | 6-3,6-2 |
| ITF M25 Johannesburg | 2021/09/12 07:30 | Munashe Chingono v Anro Nel | 1-6,2-6 |