Stadium: Court 8 Round: 19 Ground: Hardcourt outdoor
| Challenger Potchefstroom | 2021/02/07 12:30 | Lucas Miedler v Nick Chappell | 2-6,4-6 |
| UTR Pro Tennis Series Florida | 2021/01/24 14:00 | Nick Chappell v Giulio Perego | 6-1,7-5 |
| UTR Pro Tennis Series Florida | 2021/01/23 17:00 | Nick Chappell v Ronan Jachuck | 6-4,2-6,5-4 |
| UTR Pro Tennis Series Florida | 2021/01/21 18:00 | Nick Chappell v Cristian C. Rodriguez Sanchez | 3-6,4-5 |
| UTR Pro Tennis Series Florida | 2021/01/20 19:00 | Nick Chappell v Aditya Vashistha | 6-4,5-4 |
| UTR Pro Tennis Series Florida | 2021/01/19 14:00 | Nick Chappell v Daniel Milavsky | 6-2,6-5 |
| UTR Pro Tennis Series Florida | 2021/01/18 18:30 | Nick Chappell v Matt Kuhar | 6-0,5-2 |
| UTR Pro Tennis Series Florida | 2021/01/16 18:00 | Nick Chappell v Joshua Sheehy | 3-6,0-0 |
| Challenger Potchefstroom | 2021/02/07 14:05 | Devin Badenhorst v Jack Draper | 1-6,1-6 |
| Battle of the Brits | 2020/12/23 11:20 | Jack Draper v Anton Matusevich | 3-6,6-2,8-10 |
| Battle of the Brits | 2020/12/22 11:30 | Jack Draper v Jay Clarke | 6-4,6-1 |
| Battle of the Brits | 2020/12/21 13:50 | Cameron Norrie v Jack Draper | 6-7,6-7 |
| Battle of the Brits | 2020/12/20 10:00 | Jack Draper v Liam Broady | 6-7,4-6 |
| 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 |