Stadium: Court 2 Round: 25 Ground: Hardcourt outdoor
| 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 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 Ulcinj | 2021/09/01 13:30 | Antonio Cayetano March v Simon A Ivanov | 7-6,6-1 |
| ITF M25 Bacau | 2021/08/18 12:40 | Simon A Ivanov v Arthur Cazaux | 4-6,4-6 |
| ITF M25 Bacau | 2021/08/17 07:00 | Simon A Ivanov v Gheorghe Claudiu Schinteie | 6-3,6-1 |
| ITF M15 Sozopol | 2021/10/05 06:30 | George Lazarov v Nikola Keremedchiev | 6-2,6-7,3-10 |
| ITF M15 Sozopol | 2021/10/03 09:00 | Nikola Keremedchiev v James Ibrahim | 4-6,6-4,10-4 |
| ITF M15 Novi Sad | 2021/08/01 07:00 | Nikola Keremedchiev v Darko Jandric | 1-6,6-7 |