Stadium: Court 1 Round: 44 Ground: Clay
| ITF - M15 Sofia | 2021/07/04 07:30 | Andrea Picchione v Plamen Milushev | 6-7,0-6 |
| ITF - M15 Skopje | 2021/06/09 09:00 | Hanwen Li v Plamen Milushev | 6-4,6-7,6-4 |
| ITF - M15 Skopje | 2021/06/08 07:30 | Plamen Milushev v Viktor Jovic | 6-4,7-6 |
| ITF - M15 Skopje | 2021/06/07 09:30 | Plamen Milushev v Kristijan Juhas | 6-4,2-6,10-6 |
| UTR Pro Tennis Series - Pazardzhik | 2021/04/11 08:30 | Yurii Dzhavakian v Plamen Milushev | 3-6,2-6 |
| UTR Pro Tennis Series - Pazardzhik | 2021/04/10 12:00 | Plamen Milushev v Pierre Faivre | 6-7,6-2,6-4 |
| UTR Pro Tennis Series - Pazardzhik | 2021/04/09 10:30 | Yanaki Milev v Plamen Milushev | 6-3,6-7,2-6 |
| UTR Pro Tennis Series - Pazardzhik | 2021/04/08 09:15 | Constant De La Bassetiere v Plamen Milushev | 6-4,6-2 |
| ITF - M15 Sofia | 2021/07/04 07:30 | Vlad Andrei Dumitru v Leonid Sheyngezikht | 1-6,4-6 |
| ITF - M25 Belgrad | 2021/06/29 08:40 | Leonid Sheyngezikht v Dusan Milanovic | 6-3,4-6,10-12 |
| 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 |