Stadium: Court 3 Round: 27 Ground: Clay
| German Championship | 2020/12/13 10:00 | Elmar Ejupovic v Benjamin Hassan | 6-4,6-7,4-6 |
| German Championship | 2020/12/12 11:30 | Benjamin Hassan v Henri Squire | 6-3,6-4 |
| German Championship | 2020/12/11 10:30 | Jakob Schnaitter v Benjamin Hassan | 3-6,6-4,3-6 |
| German Championship | 2020/12/10 10:30 | Michael Weindl v Benjamin Hassan | 3-6,4-6 |
| German Championship | 2020/12/08 15:00 | Jim Walder v Benjamin Hassan | 2-6,6-7 |
| ITF M15 Alkmaar | 2020/08/28 14:30 | Clement Geens v Benjamin Hassan | 7-5,7-5 |
| ITF M15 Alkmaar | 2020/08/27 13:30 | Antonio Cayetano March v Benjamin Hassan | 5-7,1-6 |
| ITF M15 Alkmaar | 2020/08/25 14:30 | Constantin Schmitz v Benjamin Hassan | 4-6,6-3,3-6 |
| ITF M15 Antalya | 2020/12/04 07:00 | Flavio Cobolli v Filip Misolic | 4-6,0-6 |
| ITF M15 Antalya | 2020/12/03 10:00 | Yanki Erel v Flavio Cobolli | 3-6,2-6 |
| ITF M15 Antalya | 2020/12/02 07:00 | Martin Dimitrov v Flavio Cobolli | 0-6,4-6 |
| Challenger Parma 2 | 2020/10/31 15:30 | Tristan Lamasine v Flavio Cobolli | 6-2,6-1 |
| ITF M15 Sharm El Sheikh | 2020/10/28 13:25 | David Poljak v Flavio Cobolli | 7-6,4-6,7-5 |
| ITF M15 Sharm El Sheikh | 2020/10/23 07:00 | Pablo Vivero Gonzalez v Flavio Cobolli | 6-3,2-6,7-5 |
| ITF M15 Sharm El Sheikh | 2020/10/21 11:25 | Daniele Capecchi v Flavio Cobolli | 3-6,6-2,5-7 |
| ATP Rome | 2020/09/12 09:20 | Flavio Cobolli v Dominik Koepfer | 6-7,6-3,0-6 |