| UTR Pro Tennis Series Brasov | 2021/10/30 09:30 | Vasile Antonescu v Simon A Ivanov | 6-0,6-3 |
| UTR Pro Tennis Series Brasov | 2021/10/27 11:30 | Simon A Ivanov v Bogdan Borza | 4-6,2-5 |
| UTR Pro Tennis Series Brasov | 2021/10/26 07:00 | Simon A Ivanov v Ilya Snitari | 5-7,3-6 |
| UTR Pro Tennis Series Brasov | 2021/10/25 08:30 | Simon A Ivanov v Samuil Konov | 6-4,6-2 |
| ITF M15 Sozopol | 2021/10/13 10:00 | Simon A Ivanov v Petr Nesterov | 3-6,2-6 |
| ITF M15 Sozopol | 2021/10/07 07:00 | Tim Handel v Simon A Ivanov | 7-5,6-2 |
| ITF M15 Sozopol | 2021/10/06 07:00 | Simon A Ivanov v Nikola Keremedchiev | 6-1,1-6,6-3 |
| ATP Sofia | 2021/09/26 11:05 | Pedro Martinez v Simon A Ivanov | 7-5,6-1 |