Stadium: Court 5 Round: 19 Ground: Hardcourt outdoor
| Challenger Bratislava | 2020/11/08 12:40 | Mathias Bourgue v Jack Draper | 6-7,6-4,6-4 |
| Challenger Bratislava | 2020/11/07 18:30 | Elmar Ejupovic v Jack Draper | 2-6,6-7 |
| Challenger Parma 2 | 2020/11/02 15:05 | Frederico Ferreira Silva v Jack Draper | 6-7,6-4,7-5 |
| Challenger Parma 2 | 2020/11/01 10:00 | Evgeny Karlovskiy v Jack Draper | 3-6,0-6 |
| Challenger Parma 2 | 2020/10/31 11:20 | Lorenzo Bocchi v Jack Draper | 4-6,6-7 |
| Challenger Ismaning | 2020/10/18 09:00 | Tomas Martin Etcheverry v Jack Draper | 7-6,6-7,6-4 |
| Challenger Ismaning | 2020/10/17 09:00 | Jack Draper v Evgeny Karlovskiy | 6-1,7-5 |
| LTA British Tour | 2020/07/18 11:00 | Jack Draper v Arthur Fery | 3-6,4-6 |
| 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 |
| Tennis Point Exhibition Series | 2020/08/01 09:30 | Constantin Schmitz v Benjamin Hassan | 6-7,7-6,0-6 |
| Tennis Point Exhibition Series | 2020/07/31 09:30 | Daniel Vishnick v Benjamin Hassan | 1-6,1-6 |
| Tennis Point Exhibition Series | 2020/07/30 10:30 | Luca Gelhardt v Benjamin Hassan | 5-7,4-6 |
| Tennis Point Exhibition Series | 2020/07/29 08:00 | Hazem Naw v Benjamin Hassan | 4-6,6-7 |
| Tennis Point Exhibition Series | 2020/07/28 11:15 | Johannes Haerteis v Benjamin Hassan | 4-6,2-6 |