| 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 |
| ATP Nur-Sultan | 2021/09/19 06:00 | Simon A Ivanov v Dmitry Popko | 2-6,3-6 |
| UTR Pro Tennis Series Brasov | 2021/10/27 11:30 | Samuil Konov v Artem Podorozhnyi | 3-6,6-4,3-6 |
| UTR Pro Tennis Series Brasov | 2021/10/25 08:30 | Ilya Snitari v Artem Podorozhnyi | 6-2,6-1 |
| UTR Pro Tennis Series Mulheim | 2021/09/25 10:00 | Oleksandr Bielinskyi v Artem Podorozhnyi | 6-3,6-3 |
| UTR Pro Tennis Series Mulheim | 2021/09/24 08:00 | Edison Ambarzumjan v Artem Podorozhnyi | 1-6,3-5 |
| UTR Pro Tennis Series Mulheim | 2021/09/23 11:00 | Christos Keisidis v Artem Podorozhnyi | 5-7,2-5 |
| UTR Pro Tennis Series Mulheim | 2021/09/21 08:00 | Colin Sinclair v Artem Podorozhnyi | 5-7,4-6 |
| UTR Pro Tennis Series Mulheim | 2021/09/20 09:30 | Artem Podorozhnyi v Jurriaan Bol | 7-6,5-3 |
| ITF M15 Chornomorsk | 2021/09/03 09:10 | Artem Podorozhnyi v Illya Beloborodko | 1-6,6-7 |