Stadium: TK PALILULA C4 Round: 62 Ground: Clay
| ITF - M25 Belgrad | 2021/06/28 10:00 | Leonid Sheyngezikht v Giovanni Oradini | 3-6,6-3,10-5 |
| ITF - M25 Belgrad | 2021/06/27 09:00 | Aleksa Daskalovic v Leonid Sheyngezikht | 4-6,2-6 |
| ITF - M15 Skopje | 2021/06/08 07:30 | Petr Michnev v Leonid Sheyngezikht | 6-2,2-6,10-6 |
| ITF - M15 Skopje | 2021/06/07 08:30 | Leonid Sheyngezikht v Ondrej Horak | 6-0,7-5 |
| ITF - M15 Skopje | 2021/06/06 07:30 | Paul Valsecchi v Leonid Sheyngezikht | 6-7,4-6 |
| ITF - M15 Skopje | 2021/05/30 07:00 | Louis Allen v Leonid Sheyngezikht | 6-4,7-5 |
| ITF - M15 St Petersburg - Calificari | 2021/04/11 11:00 | Leonid Sheyngezikht v Alexander Zgirovsky | 6-4,4-6,4-10 |
| ITF - M15 St Petersburg | 2021/04/05 07:00 | Leonid Sheyngezikht v Alexandr Binda | 2-6,4-6 |
| ITF - M25 Belgrad | 2021/06/28 10:00 | Dusan Milanovic v Egor Noskin | 6-4,6-4 |
| ITF - M25 Belgrad | 2021/06/27 09:00 | Benjamin Niv v Dusan Milanovic | 3-6,4-6 |
| ITF - M15 Brcko | 2021/05/21 06:55 | Dusan Milanovic v Joao Lucas Reis da Silva | 4-6,4-6 |
| ITF - M15 Brcko | 2021/05/18 09:30 | Dusan Milanovic v Pavle Daljev | 6-0,6-4 |
| ITF - M15 Brcko | 2021/05/17 15:30 | Besir Durguti v Dusan Milanovic | 3-6,2-6 |
| ITF - M15 Brcko | 2021/05/16 12:30 | Samuel M Arjona v Dusan Milanovic | 7-6,4-6,1-10 |