| ITF - M15 Sófia | 2021/07/05 07:00 | Plamen Milushev v Leonid Sheyngezikht | 3-6,6-3,9-11 |
| ITF - M15 Sófia | 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 | 2021/07/14 10:30 | Adriano Dzhenev v Dmitrii Vasilev | 6-1,7-6 |
| UTR Pro Tennis Series - Pazardzhik | 2021/07/12 09:00 | Yanais Laurent v Dmitrii Vasilev | 2-6,6-2,6-3 |
| ITF - M15 Sófia | 2021/07/07 06:50 | Dmitrii Vasilev v Leonid Sheyngezikht | 0-6,2-6 |
| ITF - M15 Antália | 2021/06/13 07:30 | Pietro Marino v Dmitrii Vasilev | 6-1,6-1 |
| ITF - M15 Antália | 2021/06/07 13:25 | Daniel Antonio Nunez v Dmitrii Vasilev | 6-1,6-1 |
| ITF - M15 Skopje | 2021/06/06 13:30 | Dmitrii Vasilev v Taiyo Yamanaka | 3-6,6-7 |
| ITF - M15 Antália | 2021/06/06 07:30 | Dmitrii Vasilev v Efe Comu | 6-3,6-7,10-8 |
| ITF - M15 Novomoskovsk | 2021/05/31 06:15 | Alexander Zgirovsky v Dmitrii Vasilev | 6-1,6-1 |