| UTR Pro Tennis Series Sofia | 2021/08/30 07:00 | Martin Dimitrov v Samuil Konov | 4-6,6-1,5-1 |
| ITF M15 Monastir | 2021/08/09 08:30 | Rishab Agarwal v Martin Dimitrov | 6-2,6-1 |
| ITF M15 Monastir | 2021/08/08 10:30 | Masood Eisa-Beygi v Martin Dimitrov | 2-6,1-6 |
| ITF M15 Monastir | 2021/08/04 07:30 | Mateo Nicolas Martinez v Martin Dimitrov | 6-2,6-2 |
| ITF M15 Monastir | 2021/08/03 07:30 | Seita Watanabe v Martin Dimitrov | 6-7,3-6 |
| ITF M15 Monastir | 2021/08/02 08:30 | Nikita Ianin v Martin Dimitrov | 4-6,6-3,5-10 |
| ITF M15 Monastir | 2021/08/01 10:00 | Nikolas Moceanu v Martin Dimitrov | 3-6,2-6 |
| ITF M15 Sofia | 2021/07/05 08:00 | Martin Dimitrov v Mihai Razvan Marinescu | 6-3,6-7,5-10 |
| UTR Pro Tennis Series Sofia | 2021/08/30 11:15 | Matias Zukas v Ivan Penev | 7-5,6-3 |
| UTR Pro Tennis Series Sofia | 2021/08/29 12:30 | Ivan Penev v Alexandru Luca | 6-1,6-4 |
| ITF Bulgaria F1 | 2018/05/15 08:25 | Ivan Penev v Stefan Seifert | 4-6,2-6 |