Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| 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 |
| UTR Pro Tennis Series Sofia | 2021/08/30 07:00 | Martin Dimitrov v Samuil Konov | 4-6,6-1,5-1 |
| ITF M25 Skopje | 2021/10/01 12:30 | Alexander Cozbinov v Matteo Arnaldi | 0-6,1-6 |
| ITF M25 Skopje | 2021/10/01 08:15 | Alexander Cozbinov v Stefano Battaglino | 6-2,7-5 |
| ITF M25 Skopje | 2021/09/28 11:15 | Mariano Navone v Alexander Cozbinov | 6-3,5-7,1-6 |
| Challenger Istanbul | 2021/09/12 08:00 | Adrian Andreev v Alexander Cozbinov | 6-4,6-4 |
| ITF M25 Trier | 2021/08/26 09:30 | Tim Handel v Alexander Cozbinov | 6-2,3-6,6-2 |
| ITF M25 Trier | 2021/08/24 15:30 | Alexander Cozbinov v Laurent Lokoli | 6-2,3-6,7-6 |
| ITF M25 Ueberlingen | 2021/08/19 10:00 | Alexander Cozbinov v Tim Handel | 3-6,4-6 |
| ITF M25 Ueberlingen | 2021/08/18 10:10 | Jeremy Jahn v Alexander Cozbinov | 3-6,7-6,1-6 |