Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| Challenger Orlando | 2020/11/14 15:00 | Roy Smith v Nick Chappell | 6-7,1-6 |
| ITF M25 Naples | 2021/02/24 14:50 | Diego Hidalgo v Nick Chappell | 6-3,1-6,6-4 |
| Challenger Potchefstroom - selejtezők | 2021/02/14 11:20 | Jack Draper v Nick Chappell | 6-4,6-4 |
| 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 |
| ITF M15 Nur-Sultan | 2021/02/11 08:15 | Roy Smith v Mats Rosenkranz | 6-3,4-6,5-7 |
| ITF M15 Nur-Sultan | 2021/02/10 03:55 | Roy Smith v Marco Brugnerotto | 6-4,6-7,6-3 |
| ITF M15 Nur-Sultan | 2021/02/03 05:40 | Roy Smith v Matteo Donati | 7-5,4-6,6-7 |
| ITF M15 Santo Domingo | 2020/12/12 14:45 | Roy Smith v Oliver Crawford | 6-2,1-6,4-6 |
| ITF M15 Santo Domingo | 2020/12/11 13:30 | Roy Smith v Shintaro Mochizuki | 6-3,6-3 |
| ITF M15 Santo Domingo | 2020/12/10 15:25 | Roy Smith v Jurgen Briand | 7-6,6-4 |
| ITF M15 Santo Domingo | 2020/12/08 16:50 | Roy Smith v Antonio Cayetano March | 6-4,6-4 |
| ITF M15 Santo Domingo | 2020/12/03 13:30 | Leonardo Civita-Telles v Roy Smith | 6-3,6-3 |