Estádio: Hard 20 Round: 25 Ground: Hardcourt outdoor
| UTR Pro Tennis Series - Brașov | 2021/10/30 09:30 | Vasile Antonescu v Simon A Ivanov | 6-0,6-3 |
| UTR Pro Tennis Series - Brașov | 2021/10/27 11:30 | Simon A Ivanov v Bogdan Borza | 4-6,2-5 |
| UTR Pro Tennis Series - Brașov | 2021/10/26 07:00 | Simon A Ivanov v Ilya Snitari | 5-7,3-6 |
| UTR Pro Tennis Series - Brașov | 2021/10/25 08:30 | Simon A Ivanov v Samuil Konov | 6-4,6-2 |
| 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 |
| ITF - M15 Heraklion | 2021/11/01 09:00 | Michael Weindl v Ioannis Papounidis | 3-6,6-2,3-10 |
| Challenger - Ismaning | 2021/10/24 10:35 | Matthias Bachinger v Michael Weindl | 6-1,6-3 |
| ITF - M15 Allershausen | 2021/09/01 09:00 | Dominik Boehler v Michael Weindl | 1-6,6-1,6-2 |
| ITF - M15 Allershausen | 2021/08/31 08:00 | Anirudh Chandrasekar v Michael Weindl | 2-6,3-6 |
| ITF - M25 Trimbach | 2021/03/08 09:00 | Jonas Schaer v Michael Weindl | 7-6,5-7,11-9 |
| ITF - M15 Antália | 2021/01/11 07:00 | Calin Manda v Michael Weindl | 7-6,6-2 |
| ITF - M15 Antália | 2021/01/10 06:00 | Emir Sutekin v Michael Weindl | 0-6,2-6 |
| Campeonato da Alemanha | 2020/12/10 10:30 | Michael Weindl v Benjamin Hassan | 3-6,4-6 |