Stadium: Court 1 Round: 44 Ground: Hardcourt outdoor
| ITF - M15 Sozopol | 2021/09/13 07:00 | Plamen Milushev v Nikola Kolyachev | 6-4,6-3 |
| UTR Pro Tennis Series - Sofia | 2021/08/30 08:30 | Plamen Milushev v Dian Nedev | 4-6,2-5 |
| UTR Pro Tennis Series - Pazardzhik | 2021/07/18 09:00 | Yanaki Milev v Plamen Milushev | 3-6,6-6 |
| UTR Pro Tennis Series - Pazardzhik | 2021/07/17 12:00 | Iliyan Radulov v Plamen Milushev | 6-3,1-6,2-6 |
| UTR Pro Tennis Series - Pazardzhik | 2021/07/15 07:58 | Plamen Milushev v Dmitrii Vasilev | 6-1,6-0 |
| ITF - M15 Sofia | 2021/07/05 07:00 | Plamen Milushev v Leonid Sheyngezikht | 3-6,6-3,9-11 |
| 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 Sozopol | 2021/09/13 08:00 | Samuil Konov v Adrian Mateo Bejenaru | 6-4,6-4 |
| ITF - M15 Sozopol | 2021/09/12 11:00 | Samuil Konov v Denislav Prodanov | 6-2,6-0 |
| UTR Pro Tennis Series - Sofia | 2021/09/02 11:30 | Ivailo Keremedchiev v Samuil Konov | 3-6,7-6,5-2 |
| UTR Pro Tennis Series - Sofia | 2021/09/01 11:00 | Samuil Konov v Ivan Penev | 4-6,6-1,6-0 |
| UTR Pro Tennis Series - Sofia | 2021/08/31 06:30 | Samuil Konov v Matias Zukas | 3-6,1-6 |
| UTR Pro Tennis Series - Sofia | 2021/08/30 07:00 | Martin Dimitrov v Samuil Konov | 4-6,6-1,5-1 |
| ITF - M15 Curtea de Arges | 2021/08/08 10:00 | Dan Alexandru Tomescu v Samuil Konov | 6-1,6-3 |
| ITF - M25 Pitesti | 2021/08/01 13:30 | Martin Zeljenka v Samuil Konov | 6-4,6-4 |