Stadium: Centre Court Round: 26 Ground: Clay
| Challenger St. Petersburg | 2021/03/08 10:00 | Rudolf Molleker v Evgeny Karlovskiy | 6-3,7-5 |
| Challenger Rennes | 2019/01/22 09:00 | Evgeny Karlovskiy v Rudolf Molleker | 6-4,6-2 |
| Challenger Rome Qual | 2021/04/26 09:30 | Felipe Meligeni Rodrigues Alves v Evgeny Karlovskiy | 6-4,6-1 |
| Challenger Rome Qual | 2021/04/25 08:00 | Viktor Galovic v Evgeny Karlovskiy | 3-6,4-6 |
| Challenger Split Qual | 2021/04/11 09:00 | Evgeny Karlovskiy v Matteo Viola | 2-6,2-6 |
| ITF M25 Biel | 2021/04/01 12:00 | Alexis Gautier v Evgeny Karlovskiy | 6-4,7-5 |
| ITF M25 Biel | 2021/03/31 09:25 | Gijs Brouwer v Evgeny Karlovskiy | 3-6,7-5,6-7 |
| Challenger Lugano | 2021/03/26 11:00 | Yuichi Sugita v Evgeny Karlovskiy | 7-6,4-6,7-6 |
| Challenger Lugano | 2021/03/24 15:50 | Evgeny Karlovskiy v Akira Santillan | 6-4,6-3 |
| Challenger Lugano | 2021/03/23 09:30 | Jelle Sels v Evgeny Karlovskiy | 2-6,6-1,1-6 |
| Challenger Ostrava | 2021/04/26 09:30 | Rudolf Molleker v Lukas Klein | 3-6,1-6 |
| Challenger Ostrava | 2021/04/25 11:40 | Rudolf Molleker v Dalibor Svrcina | 6-4,2-6,6-3 |
| ITF M25 Meerbusch | 2021/04/14 14:35 | Rudolf Molleker v Elmar Ejupovic | 6-7,6-4,3-6 |
| Challenger St. Petersburg | 2021/03/10 13:20 | Rudolf Molleker v Jiri Lehecka | 2-6,3-6 |
| Challenger St. Petersburg | 2021/03/08 10:00 | Rudolf Molleker v Evgeny Karlovskiy | 6-3,7-5 |
| Challenger St. Petersburg | 2021/03/02 07:00 | Rudolf Molleker v Viktor Durasovic | 6-7,4-6 |
| Challenger Antalya Qual | 2021/01/31 08:40 | Rudolf Molleker v Andrea Arnaboldi | 6-3,7-5 |
| Challenger Antalya | 2021/01/28 11:30 | Rudolf Molleker v Tommy Robredo | 3-6,4-6 |