| UTR Pro Tennis Series Nis | 2021/10/10 08:00 | Christos Keisidis v Vladimir Popov | 6-1,5-2 |
| UTR Pro Tennis Series Nis | 2021/10/09 13:15 | Aleksandar Ljubojevic v Vladimir Popov | 4-6,5-7 |
| UTR Pro Tennis Series Nis | 2021/10/08 18:15 | Petar Pjevcevic v Vladimir Popov | 2-6,6-0,5-1 |
| UTR Pro Tennis Series Nis | 2021/10/07 14:00 | Duje Kekez v Vladimir Popov | 6-0,5-1 |
| UTR Pro Tennis Series Nis | 2021/10/05 10:30 | Ivan Denisov v Vladimir Popov | 6-2,5-4 |
| UTR Pro Tennis Series Nis | 2021/10/04 08:30 | Vladimir Popov v Lazar Radenkovic | 6-1,5-2 |
| UTR Pro Tennis Series Sofia | 2021/09/02 07:00 | Vladimir Popov v Christos Keisidis | 7-6,6-7,3-6 |
| UTR Pro Tennis Series Sofia | 2021/09/01 11:00 | Mick Lescure v Vladimir Popov | 1-6,4-6 |
| 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 |
| 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 |