Estadio: Court 1 Round: 19 Ground: Clay
| Challenger de Tulln | 2021/09/05 09:00 | Benjamin Hassan v Lukas Krainer | 6-4,6-4 |
| Challenger de Barletta | 2021/08/22 10:00 | Cristian Cristian Rodríguez v Benjamin Hassan | 6-2,4-6,6-2 |
| Challenger de 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 |
| Challenger de Braunschweig | 2021/07/08 13:00 | Marvin Moeller v Benjamin Hassan | 6-4,6-2 |
| Challenger de Braunschweig | 2021/07/07 12:55 | Sandro Ehrat v Benjamin Hassan | 6-4,3-6,4-6 |
| Challenger de Braunschweig | 2021/07/06 10:30 | Benjamin Hassan v Dayne Kelly | 6-4,7-6 |
| Challenger de Braunschweig | 2021/07/05 12:55 | Benjamin Hassan v Mats Rosenkranz | 2-6,2-6 |
| Challenger de Tulln | 2021/09/05 09:00 | Nicholas David Ionel v Bogdan Bobrov | 1-6,1-6 |
| Challenger de St. Tropez | 2021/09/02 09:00 | Thanasi Kokkinakis v Bogdan Bobrov | 6-0,6-2 |
| Challenger de St. Tropez | 2021/08/31 12:15 | Bogdan Bobrov v Zizou Bergs | 6-4,7-5 |
| Challenger de St. Tropez | 2021/08/30 09:00 | Bogdan Bobrov v Daniil Glinka | 7-6,6-3 |
| Challenger de Varsovia | 2021/08/23 09:00 | Alexander Shevchenko v Bogdan Bobrov | 6-3,6-1 |
| Challenger de Varsovia | 2021/08/22 10:30 | Vladyslav Manafov v Bogdan Bobrov | 7-6,4-6,3-6 |
| Challenger de Luedenscheid | 2021/08/16 09:30 | Genaro Alberto Olivieri v Bogdan Bobrov | 6-1,6-2 |
| Challenger de Luedenscheid | 2021/08/15 09:30 | Bogdan Bobrov v Johannes Haerteis | 1-6,6-4,6-3 |