| UTR Pro Tennis Series Pazardzhik | 2021/04/02 11:30 | Martin Dimitrov v Eric Vanshelboim | 0-6,2-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/01 12:00 | Martin Dimitrov v Alexander Lazov | 0-6,1-6 |
| ITF M15 Antalya | 2020/12/22 06:30 | Martin Dimitrov v Umut Akkoyun | 6-3,3-6,7-10 |
| ITF M15 Antalya | 2020/12/21 10:50 | Martin Dimitrov v Efe Comu | 7-5,6-3 |
| ITF M15 Antalya | 2020/12/06 07:00 | Martin Dimitrov v Timur Kiyamov | 3-6,6-2,11-13 |
| ITF M15 Antalya | 2020/12/02 07:00 | Martin Dimitrov v Flavio Cobolli | 0-6,4-6 |
| ITF M15 Antalya | 2020/12/01 07:00 | Timur Kiyamov v Martin Dimitrov | 4-6,1-6 |
| ITF M15 Antalya | 2020/11/30 12:30 | Suleyman Deniz Gursoy v Martin Dimitrov | 1-6,0-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/02 08:30 | Dinko Dinev v Simon A Ivanov | 6-2,5-0 |
| UTR Pro Tennis Series Pazardzhik | 2021/03/29 08:00 | Simon A Ivanov v Dragos Dima | 2-6,4-5 |
| ITF M15 Antalya | 2021/02/14 12:00 | Simon A Ivanov v Damien Wenger | 6-2,2-6,6-10 |
| ITF M15 Antalya | 2021/02/02 07:00 | Mathys Erhard v Simon A Ivanov | 7-6,6-2 |
| ITF M15 Antalya | 2021/01/31 06:30 | Onder Balci v Simon A Ivanov | 1-6,2-6 |
| ITF M15 Antalya | 2021/01/28 08:00 | Leopold Zima v Simon A Ivanov | 6-4,7-5 |
| ITF M15 Curtea de Arges | 2020/09/15 12:05 | Duje Ajdukovic v Simon A Ivanov | 6-2,6-1 |
| ITF M15 Sharm El Sheikh | 2020/03/04 13:55 | Simon A Ivanov v Kelsey Stevenson | 4-6,4-6 |