Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| 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 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 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 |
| Challenger Segovia | 2021/07/26 09:00 | Alexander Cozbinov v Dalibor Svrcina | 1-6,6-2,2-6 |
| Challenger Segovia | 2021/07/25 09:00 | Federico Zeballos v Alexander Cozbinov | 1-6,1-6 |
| ITF M25 Idanha-A-Nova | 2021/07/22 08:00 | Alexander Cozbinov v Nicolas Moreno De Alboran | 6-3,6-7,6-7 |
| ITF M25 Idanha-A-Nova | 2021/07/21 11:35 | Alexander Cozbinov v Mehluli D A Sibanda | 6-3,6-0 |