Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| ITF - Sozopol M15 | 2021/10/07 07:00 | Tim Handel v Simon A Ivanov | 7-5,6-2 |
| ITF - Sozopol M15 | 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 |
| ITF - Sozopol M15 | 2021/09/16 08:00 | Simon A Ivanov v George Tsivadze | 7-6,6-0 |
| ITF - Sozopol M15 | 2021/09/15 09:30 | Simon A Ivanov v Dragomir Draganov | 6-2,6-4 |
| ITF - Ulcinj M15 | 2021/09/07 08:00 | Felix Gill v Simon A Ivanov | 6-3,5-7,7-6 |
| ITF - Ulcinj M15 | 2021/09/01 13:30 | Antonio Cayetano March v Simon A Ivanov | 7-6,6-1 |
| ITF - Sozopol M15 | 2021/10/05 10:00 | Alexandar Lazarov v Petr Nesterov | 6-1,6-1 |
| ITF - Sozopol M15 | 2021/09/16 10:05 | Tommaso Compagnucci v Petr Nesterov | 6-2,6-0 |
| ITF - Sozopol M15 | 2021/09/15 07:00 | Petr Nesterov v Caspar Schuetze | 6-1,6-3 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/15 06:00 | Petr Nesterov v Valentin Vanta | 6-2,6-3 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/14 09:00 | Petr Nesterov v Yurii Dzhavakian | 7-6,6-4 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/13 07:30 | Petr Nesterov v Alexander Lazov | 6-4,5-3 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/12 10:30 | Petr Nesterov v Arthus De La Bassetiere | 6-3,7-5 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/09 12:30 | Petr Nesterov v Ilya Snitari | 2-6,3-6 |