Stadium: Court 2 Round: 44 Ground: Hardcourt outdoor
| ITF M15 Sozopol | 2021/10/06 09:35 | Martin Dimitrov v Alexander Cozbinov | 1-6,3-6 |
| ITF M15 Sozopol | 2021/10/05 06:30 | Vlad Stoica v Martin Dimitrov | 1-6,2-6 |
| ITF M15 Sozopol | 2021/10/04 07:00 | Suleyman Deniz Gursoy v Martin Dimitrov | 2-6,1-6 |
| ITF M15 Sozopol | 2021/09/15 07:00 | Martin Dimitrov v Calin Manda | 4-6,4-6 |
| ITF M15 Sozopol | 2021/09/13 07:00 | Martin Dimitrov v Radoslav Shandarov | 6-7,6-2,14-12 |
| UTR Pro Tennis Series Sofia | 2021/09/02 07:00 | Martin Dimitrov v Dian Nedev | 3-6,3-5 |
| UTR Pro Tennis Series Sofia | 2021/09/01 11:00 | Martin Dimitrov v Matias Zukas | 0-6,2-5 |
| UTR Pro Tennis Series Sofia | 2021/08/31 06:30 | Martin Dimitrov v Ivan Penev | 1-6,6-3,6-3 |
| ITF M15 Sozopol | 2021/10/04 08:00 | Dragos Petre Popeanga v Matic Dimic | 1-6,3-6 |
| ITF M25 Bacau | 2021/08/17 10:10 | Oleksii Krutykh v Dragos Petre Popeanga | 6-0,6-1 |
| ITF M15 Curtea de Arges | 2021/08/08 08:00 | Dragos Petre Popeanga v Dan Radu Munteanu | 2-6,1-6 |
| ITF M25 Pitesti | 2021/08/01 10:00 | Dragos Petre Popeanga v Mihai Razvan Marinescu | 3-6,0-6 |
| ITF M15 Bucharest | 2021/05/24 09:30 | Dragos Petre Popeanga v Bogdan Borza | 3-6,3-6 |
| ITF M15 Curtea de Arges | 2020/09/13 09:00 | Michalis Sakellaridis v Dragos Petre Popeanga | 6-4,7-5 |