Stadium: Court 1 Round: 62 Ground: Clay
| UTR Pro Tennis Series Pazardzhik | 2021/04/04 10:00 | Yurii Dzhavakian v Simon A Ivanov | 6-2,6-4 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/03 11:30 | Martin Dimitrov v Simon A Ivanov | 7-5,2-6,1-5 |
| 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 |