Stadium: Court 2 Round: 26 Ground: Hardcourt outdoor
| Challenger Cleveland | 2021/03/16 19:10 | Nick Chappell v Roy Smith | 4-6,7-5,4-6 |
| Challenger Orlando | 2020/11/14 15:00 | Roy Smith v Nick Chappell | 6-7,1-6 |
| Challenger Santiago | 2021/10/11 17:15 | Nick Chappell v Hernan Casanova | 3-6,4-6 |
| Challenger Santiago | 2021/10/06 16:00 | Nick Chappell v Sebastian Baez | 7-5,4-6,1-6 |
| Challenger Santiago | 2021/10/04 22:55 | Diego F Flores v Nick Chappell | 3-6,6-3,5-7 |
| Challenger Istanbul | 2021/09/14 11:15 | Alexandre Muller v Nick Chappell | 6-4,6-2 |
| Challenger Istanbul | 2021/09/13 07:30 | Nick Chappell v Alexander Shevchenko | 6-4,6-2 |
| Challenger Istanbul | 2021/09/12 09:20 | Nick Chappell v Danylo Kalenichenko | 7-6,6-4 |
| Challenger Kyiv | 2021/09/06 11:25 | Nick Chappell v Oleksii Krutykh | 3-6,6-3,1-6 |
| Challenger Mallorca | 2021/09/02 14:30 | Tobias Kamke v Nick Chappell | 6-2,6-4 |
| ITF M15 Cancun | 2021/10/12 17:00 | Roy Smith v Jesse Flores | 4-6,2-6 |
| ITF M15 Ithaca | 2021/10/06 18:35 | Roy Smith v Ryan Shane | 5-7,3-6 |
| ITF M15 Castelo Branco | 2021/07/29 14:05 | Clement Chidekh v Roy Smith | 6-4,7-5 |
| ITF M15 Castelo Branco | 2021/07/28 15:30 | Ben Jones v Roy Smith | 1-6,4-6 |
| ITF M25 Idanha-A-Nova | 2021/07/22 08:00 | Gilbert S K Junior v Roy Smith | 6-3,6-2 |
| ITF M25 Idanha-A-Nova | 2021/07/14 11:05 | Roy Smith v Tiago Cacao | 5-7,6-3,6-7 |
| ITF M15 Champaign | 2021/06/23 21:50 | Roy Smith v Thomaz Bellucci | 6-7,3-6 |
| ITF M25 Santo Domingo | 2021/06/05 16:15 | Roy Smith v Aidan Mchugh | 6-3,3-6,1-6 |