Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Sozopol | 2021/10/05 06:30 | Stoica, Vlad v Dimitrov, Martin | 1-6,2-6 |
| ITF M15 Sozopol | 2021/10/04 07:00 | Suleyman Deniz Gursoy v Dimitrov, Martin | 2-6,1-6 |
| ITF M15 Sozopol | 2021/09/15 07:00 | Dimitrov, Martin v Manda, Calin | 4-6,4-6 |
| ITF M15 Sozopol | 2021/09/13 07:00 | Dimitrov, Martin v Shandarov, Radoslav | 6-7,6-2,14-12 |
| UTR Pro Tennis Series Sofia | 2021/09/02 07:00 | Dimitrov, Martin v Dian Nedev | 3-6,3-5 |
| UTR Pro Tennis Series Sofia | 2021/09/01 11:00 | Dimitrov, Martin v Zukas, Matias | 0-6,2-5 |
| UTR Pro Tennis Series Sofia | 2021/08/31 06:30 | Dimitrov, Martin v Penev, Ivan | 1-6,6-3,6-3 |
| UTR Pro Tennis Series Sofia | 2021/08/30 07:00 | Dimitrov, Martin v Samuil Konov | 4-6,6-1,5-1 |
| ITF M25 Skopje | 2021/10/01 12:30 | Cozbinov, Alexander v Matteo Arnaldi | 0-6,1-6 |
| ITF M25 Skopje | 2021/10/01 08:15 | Cozbinov, Alexander v Battaglino, Stefano | 6-2,7-5 |
| ITF M25 Skopje | 2021/09/28 11:15 | Mariano Navone v Cozbinov, Alexander | 6-3,5-7,1-6 |
| Istanbul, Turkey | 2021/09/12 08:00 | Adrian Andreev v Cozbinov, Alexander | 6-4,6-4 |
| ITF M25 Trier | 2021/08/26 09:30 | Tim Handel v Cozbinov, Alexander | 6-2,3-6,6-2 |
| ITF M25 Trier | 2021/08/24 15:30 | Cozbinov, Alexander v Laurent Lokoli | 6-2,3-6,7-6 |
| ITF M25 Ueberlingen | 2021/08/19 10:00 | Cozbinov, Alexander v Tim Handel | 3-6,4-6 |
| ITF M25 Ueberlingen | 2021/08/18 10:10 | Jahn, Jeremy v Cozbinov, Alexander | 3-6,7-6,1-6 |