| 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 - Sófia | 2021/09/26 11:05 | Pedro Martinez v Simon A Ivanov | 7-5,6-1 |
| ATP - Nur-Sultã | 2021/09/19 06:00 | Simon A Ivanov v Dmitry Popko | 2-6,3-6 |
| ITF - M15 Sozopol | 2021/09/16 08:00 | Simon A Ivanov v George Tsivadze | 7-6,6-0 |
| ITF - M15 Sozopol | 2021/09/15 09:30 | Simon A Ivanov v Dragomir Draganov | 6-2,6-4 |
| ITF - M15 Ulcinj | 2021/09/07 08:00 | Felix Gill v Simon A Ivanov | 6-3,5-7,7-6 |
| ITF - M15 Sozopol | 2021/10/11 09:00 | Yann Wojcik v Samuil Konov | 6-1,6-2 |
| ITF - M15 Sozopol | 2021/10/10 10:30 | Enes Donmezer v Samuil Konov | 5-7,1-6 |
| ITF - M15 Sozopol | 2021/10/04 07:00 | Samuil Konov v Michael Gloeckler | 3-6,4-6 |
| ITF - M15 Pirot | 2021/09/20 11:00 | Samuil Konov v Kristijan Juhas | 3-6,5-7 |
| ITF - M15 Sozopol | 2021/09/14 07:00 | Plamen Milushev v Samuil Konov | 6-4,6-3 |
| ITF - M15 Sozopol | 2021/09/13 08:00 | Samuil Konov v Adrian Mateo Bejenaru | 6-4,6-4 |
| ITF - M15 Sozopol | 2021/09/12 11:00 | Samuil Konov v Denislav Prodanov | 6-2,6-0 |
| UTR Pro Tennis Series - Sófia | 2021/09/02 11:30 | Ivailo Keremedchiev v Samuil Konov | 3-6,7-6,5-2 |