Stadium: Court 8 Round: 14 Ground: Hardcourt outdoor
| Challenger - Potchefstroom | 2021/02/08 09:00 | Nick Chappell v Jack Draper | 6-3,6-4 |
| Challenger - Potchefstroom | 2021/02/08 09:00 | Nick Chappell v Jack Draper | 6-3,6-4 |
| 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 - Potchefstroom | 2021/02/13 09:00 | Nick Chappell v Benjamin Bonzi | 1-6,2-6 |
| Challenger - Potchefstroom | 2021/02/12 09:00 | Peter Polansky v Nick Chappell | 4-6,7-6,4-6 |
| Challenger - Potchefstroom | 2021/02/10 08:00 | Nick Chappell v Hugo Grenier | 6-2,6-4 |
| Challenger - Potchefstroom | 2021/02/09 08:00 | Nick Chappell v Nicola Kuhn | 6-1,2-6,7-6 |
| Challenger - Potchefstroom | 2021/02/08 09:00 | Nick Chappell v Jack Draper | 6-3,6-4 |
| 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 |