Stadium: Court 1 Round: 62 Ground: Clay
| UTR Pro Tennis Series Pazardzhik | 2021/04/04 10:00 | Dzhavakian, Yurii v Ivanov, Simon Anthony | 6-2,6-4 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/03 11:30 | Dimitrov, Martin v Ivanov, Simon Anthony | 7-5,2-6,1-5 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/02 08:30 | Dinko Dinev v Ivanov, Simon Anthony | 6-2,5-0 |
| UTR Pro Tennis Series Pazardzhik | 2021/03/29 08:00 | Ivanov, Simon Anthony v Dima, Dragos | 2-6,4-5 |
| ITF - M15 Antalya | 2021/02/14 12:00 | Ivanov, Simon Anthony v Damien Wenger | 6-2,2-6,6-10 |
| ITF - M15 Antalya | 2021/02/02 07:00 | Mathys Erhard v Ivanov, Simon Anthony | 7-6,6-2 |
| ITF - M15 Antalya | 2021/01/31 06:30 | Onder Balci v Ivanov, Simon Anthony | 1-6,2-6 |
| ITF - M15 Antalya | 2021/01/28 08:00 | Leopold Zima v Ivanov, Simon Anthony | 6-4,7-5 |