Stadion: Court 6 Round: 25 Ground: Clay
| UTR Pro Tennis Series - Barcelona | 2021/12/15 10:00 | Simon A Ivanov v Kuzey Cekirge | 1-6,3-6 |
| UTR Pro Tennis Series - Barcelona | 2021/12/13 09:30 | Vladimir Popov v Simon A Ivanov | 6-2,3-6,1-6 |
| UTR Pro Tennis Series - Bukarest | 2021/12/05 09:30 | Simon A Ivanov v Edris Fetisleam | 3-6,4-6 |
| UTR Pro Tennis Series - Bukarest | 2021/12/04 11:00 | Gabriel Donev v Simon A Ivanov | 6-4,3-6,1-6 |
| UTR Pro Tennis Series - Bukarest | 2021/12/03 11:00 | Dragos Constantin Ignat v Simon A Ivanov | 0-6,1-5 |
| UTR Pro Tennis Series - Bukarest | 2021/12/02 09:30 | Stefan Palosi v Simon A Ivanov | 6-7,6-4,6-4 |
| UTR Pro Tennis Series - Bukarest | 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 - Kairo | 2022/01/21 10:40 | Daniel Michalski v Denis Klok | 3-6,6-0,6-3 |
| ITF - M15 - Kairo | 2022/01/20 09:25 | Denis Klok v Lukas Krainer | 6-4,6-0 |
| ITF - M15 - Kairo | 2022/01/19 09:50 | Noah Perfetti v Denis Klok | 1-6,1-6 |
| ITF - M15 - Kairo | 2022/01/15 08:30 | Daniel Michalski v Denis Klok | 1-6,6-2,6-3 |
| ITF - M15 - Kairo | 2022/01/13 08:30 | Denis Klok v Alexandr Binda | 7-5,4-6,6-3 |
| ITF - M15 - Kairo | 2022/01/12 11:55 | Denis Klok v Caspar Schuetze | 6-1,6-1 |
| ITF - M15 - Kairo | 2022/01/08 11:00 | Denis Klok v Andrey Chepelev | 6-3,2-6,0-6 |
| ITF - M15 - Kairo | 2022/01/07 11:50 | Benjamin Lock v Denis Klok | 3-6,4-6 |