| 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 Skopje | 2021/06/08 07:30 | Plamen Milushev v Viktor Jovic | 6-4,7-6 |
| UTR Pro Tennis Series - Sofia | 2021/08/30 13:30 | Ivailo Keremedchiev v Alexandar Lazarov | 1-6,6-6 |
| UTR Pro Tennis Series - Sofia | 2021/08/29 12:30 | Mihael Mihaylov v Alexandar Lazarov | 0-6,3-6 |
| ITF - M25 Bacau | 2021/08/20 13:00 | Alexandar Lazarov v Arthur Cazaux | 6-7,4-6 |
| ITF - M25 Bacau | 2021/08/19 15:35 | Alexandar Lazarov v Dan Alexandru Tomescu | 6-2,6-4 |
| ITF - M25 Bacau | 2021/08/18 11:25 | Alexandar Lazarov v Victor Vlad Cornea | 6-4,6-4 |
| ITF - M25 Telavi | 2021/08/01 06:00 | Alessandro Ingarao v Alexandar Lazarov | 2-6,2-6 |
| ITF - M25 Telavi | 2021/07/31 13:50 | Zura Tkemaladze v Alexandar Lazarov | 2-6,1-6 |
| ITF - M25 Telavi | 2021/07/31 09:15 | Julian Cash v Alexandar Lazarov | 3-6,3-6 |