| UTR Pro Tennis Series Pazardzhik | 2021/07/16 07:30 | Iliyan Radulov v Ilya Snitari | 3-6,2-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/15 10:30 | Iliyan Radulov v Denislav Prodanov | 2-6,2-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/14 06:00 | Dian Nedev v Iliyan Radulov | 7-5,6-1 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/13 09:00 | Aristotelis Thanos v Iliyan Radulov | 4-2 |
| 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 |
| 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 |