| 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 Heraklion | 2020/11/17 07:30 | Vasil Kirkov v Billy Harris | 4-6,6-0,10-7 |
| ITF M15 Heraklion | 2020/11/16 08:00 | Sebastian Gima v Billy Harris | 1-6,1-6 |
| ITF M15 Heraklion | 2020/11/15 08:00 | Neil Oberleitner v Billy Harris | 6-2,4-6,9-11 |
| ITF M15 Heraklion | 2020/11/11 09:30 | Aristotelis Thanos v Billy Harris | 7-6,6-4 |
| ITF M15 Heraklion | 2020/11/08 12:00 | Billy Harris v Naoki Tajima | 5-7,6-1,10-7 |
| ITF M15 Heraklion | 2020/11/01 12:00 | Gabriel Donev v Billy Harris | 3-6,6-1,10-7 |
| LTA British Tour | 2020/10/04 10:45 | Anton Matusevich v Billy Harris | 6-2,6-3 |
| LTA British Tour | 2020/10/03 13:30 | Julian Cash v Billy Harris | 6-7,3-6 |