Stadium: Court 1 Round: 44 Ground: Hardcourt outdoor
| UTR Pro Tennis Series - Sofia | 2021/08/30 08:30 | Plamen Milushev v Dian Nedev | 4-6,2-5 |
| UTR Pro Tennis Series - Pazardzjik | 2021/07/18 09:00 | Yanaki Milev v Plamen Milushev | 3-6,6-6 |
| UTR Pro Tennis Series - Pazardzjik | 2021/07/17 12:00 | Iliyan Radulov v Plamen Milushev | 6-3,1-6,2-6 |
| UTR Pro Tennis Series - Pazardzjik | 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 M25 - Pitesti | 2021/08/02 06:00 | Nikola Kolyachev v Cosmin Ontica | 7-5,0-6,4-10 |
| ITF M15 Sofia | 2021/07/05 07:00 | Franco Roncadelli v Nikola Kolyachev | 6-4,6-1 |
| ITF M15 Sofia | 2021/07/04 07:30 | Nikola Kolyachev v Francisco Llanes | 6-2,6-7,10-1 |