Stadium: Hard 20 Round: 25 Ground: Hardcourt outdoor
| UTR Pro Tennis Series Brasov | 2021/10/30 09:30 | Antonescu, Vasile v Ivanov, Simon Anthony | 6-0,6-3 |
| UTR Pro Tennis Series Brasov | 2021/10/27 11:30 | Ivanov, Simon Anthony v Borza, Bogdan | 4-6,2-5 |
| UTR Pro Tennis Series Brasov | 2021/10/26 07:00 | Ivanov, Simon Anthony v Ilya Snitari | 5-7,3-6 |
| UTR Pro Tennis Series Brasov | 2021/10/25 08:30 | Ivanov, Simon Anthony v Samuil Konov | 6-4,6-2 |
| ITF M15 Sozopol | 2021/10/13 10:00 | Ivanov, Simon Anthony v Petr Nesterov | 3-6,2-6 |
| ITF M15 Sozopol | 2021/10/07 07:00 | Tim Handel v Ivanov, Simon Anthony | 7-5,6-2 |
| ITF M15 Sozopol | 2021/10/06 07:00 | Ivanov, Simon Anthony v Nikola Keremedchiev | 6-1,1-6,6-3 |
| Sofia, Bulgaria | 2021/09/26 11:05 | Pedro Martinez v Ivanov, Simon Anthony | 7-5,6-1 |
| ITF - M15 Héraklion | 2021/11/01 09:00 | Weindl, Michael v Papounidis, Ioannis | 3-6,6-2,3-10 |
| Challenger Ismaning | 2021/10/24 10:35 | Bachinger, Matthias v Weindl, Michael | 6-1,6-3 |
| ITF M15 Allershausen | 2021/09/01 09:00 | Boehler, Dominik v Weindl, Michael | 1-6,6-1,6-2 |
| ITF M15 Allershausen | 2021/08/31 08:00 | Chandrasekar, Anirudh v Weindl, Michael | 2-6,3-6 |
| ITF - M25 Trimbach | 2021/03/08 09:00 | Jonas Schaer v Weindl, Michael | 7-6,5-7,11-9 |
| ITF - M15 Antalya | 2021/01/11 07:00 | Manda, Calin v Weindl, Michael | 7-6,6-2 |
| ITF - M15 Antalya | 2021/01/10 06:00 | Sutekin, Emir v Weindl, Michael | 0-6,2-6 |
| German Championship | 2020/12/10 10:30 | Weindl, Michael v Benjamin Hassan | 3-6,4-6 |