| ITF - M15 Sozopol | 2019/05/07 10:00 | Plamen Milushev v Dian Nedev | 6-2,6-2 |
| 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 |
| ITF - M15 Skopje | 2021/06/07 09:30 | Plamen Milushev v Kristijan Juhas | 6-4,2-6,10-6 |
| UTR Pro Tennis Series - Pazardzhik | 2021/07/17 07:30 | Aleksandr Braynin v Dian Nedev | 6-3,6-2 |
| UTR Pro Tennis Series - Pazardzhik | 2021/07/15 10:30 | Dian Nedev v Ilya Snitari | 4-6,6-4,1-6 |
| 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 | Dian Nedev v Denislav Prodanov | 6-7,4-5 |
| UTR Pro Tennis Series - Pazardzhik | 2021/07/12 07:30 | Dian Nedev v Aristotelis Thanos | 6-4,5-4 |
| ITF - M15 Antalya | 2021/06/21 11:35 | Dian Nedev v Filip Duda | 4-6,2-6 |
| ITF - M15 Antalya | 2021/06/20 07:00 | Jason Janis v Dian Nedev | 2-6,2-6 |
| ITF - M15 Antalya | 2021/06/15 09:45 | Dian Nedev v Pietro Marino | 2-6,6-7 |