Stadium: Estadio CIF Round: 19 Ground: Clay
| Challenger Tulln | 2021/09/06 08:00 | Benjamin Hassan v Bogdan Bobrov | 6-4,6-4 |
| Challenger Lisbon | 2021/09/26 15:45 | Kaichi Uchida v Bogdan Bobrov | 6-7,4-6 |
| Challenger Braga | 2021/09/19 09:00 | Dalibor Svrcina v Bogdan Bobrov | 7-5,6-1 |
| Challenger Szczecin | 2021/09/13 11:05 | Vitaliy Sachko v Bogdan Bobrov | 4-6,6-3,6-4 |
| Challenger Szczecin | 2021/09/12 14:45 | Karol Drzewiecki v Bogdan Bobrov | 2-6,4-6 |
| Challenger Tulln | 2021/09/06 08:00 | Benjamin Hassan v Bogdan Bobrov | 6-4,6-4 |
| Challenger Tulln | 2021/09/05 09:00 | Nicholas David Ionel v Bogdan Bobrov | 1-6,1-6 |
| Challenger St. Tropez | 2021/09/02 09:00 | Thanasi Kokkinakis v Bogdan Bobrov | 6-0,6-2 |
| Challenger St. Tropez | 2021/08/31 12:15 | Bogdan Bobrov v Zizou Bergs | 6-4,7-5 |
| Challenger Lisbon | 2021/09/26 14:20 | Henrique Rocha v Benjamin Hassan | 4-6,2-6 |
| Davis Cup | 2021/09/18 08:45 | Benjamin Hassan v Orlando Luz | 4-6,4-6 |
| Challenger Tulln | 2021/09/07 08:00 | Sebastian Ofner v Benjamin Hassan | 6-3,5-7,7-6 |
| Challenger Tulln | 2021/09/06 08:00 | Benjamin Hassan v Bogdan Bobrov | 6-4,6-4 |
| Challenger Tulln | 2021/09/05 09:00 | Benjamin Hassan v Lukas Krainer | 6-4,6-4 |
| Challenger Barletta | 2021/08/22 10:00 | Cristian Rodriguez v Benjamin Hassan | 6-2,4-6,6-2 |
| Challenger Meerbusch | 2021/08/08 09:10 | Marvin Moeller v Benjamin Hassan | 5-7,7-5,6-3 |
| ITF M25 Wetzlar | 2021/08/03 16:10 | Henri Squire v Benjamin Hassan | 6-2,6-3 |