| UTR Pro Tennis Series Barcelona | 2021/12/12 11:30 | Vladimir Popov v Martin Dimitrov | 4-6,4-6 |
| UTR Pro Tennis Series Barcelona | 2021/12/12 08:00 | Vladimir Popov v Michalis Sakellaridis | 0-6,1-6 |
| UTR Pro Tennis Series Barcelona | 2021/12/11 08:00 | Pol Toledo Bague v Vladimir Popov | 6-4,3-2 |
| UTR Pro Tennis Series Barcelona | 2021/12/10 11:00 | Vladimir Popov v Alen Rogic-Hadzalic | 2-6,4-6 |
| UTR Pro Tennis Series Barcelona | 2021/12/08 16:32 | Vladimir Popov v Olexiy Kolisnyk | 4-6,2-6 |
| UTR Pro Tennis Series - Zadar | 2021/11/19 15:03 | Olexiy Kolisnyk v Vladimir Popov | 6-0,6-4 |
| UTR Pro Tennis Series - Zadar | 2021/11/18 12:00 | Robert Rumler v Vladimir Popov | 6-2,5-1 |
| UTR Pro Tennis Series - Zadar | 2021/11/16 12:00 | Valerii Naumenko v Vladimir Popov | 3-6,3-6 |
| UTR Pro Tennis Series - Bukurešť | 2021/12/05 09:30 | Simon A Ivanov v Edris Fetisleam | 3-6,4-6 |
| UTR Pro Tennis Series - Bukurešť | 2021/12/04 11:00 | Gabriel Donev v Simon A Ivanov | 6-4,3-6,1-6 |
| UTR Pro Tennis Series - Bukurešť | 2021/12/03 11:00 | Dragos Constantin Ignat v Simon A Ivanov | 0-6,1-5 |
| UTR Pro Tennis Series - Bukurešť | 2021/12/02 09:30 | Stefan Palosi v Simon A Ivanov | 6-7,6-4,6-4 |
| UTR Pro Tennis Series - Bukurešť | 2021/12/01 12:30 | Dan Alexandru Tomescu v Simon A Ivanov | 6-3,6-2 |
| ITF - M15 Heraklion | 2021/11/17 11:20 | Kai Wehnelt v Simon A Ivanov | 5-7,4-6 |
| ITF - M15 Heraklion | 2021/11/16 07:00 | Simon A Ivanov v Gianluca Coloma-Heck | 6-1,6-2 |
| ITF - M15 Heraklion | 2021/11/15 08:00 | Simon A Ivanov v Thomas George Brun | 6-2,6-0 |