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 Segovia | 2021/07/25 14:00 | Luca Vanni v Nick Chappell | 6-1,6-2 |
| Challenger Nur-Sultan | 2021/07/23 05:00 | Oleksii Krutykh v Nick Chappell | 3-6,6-3,7-5 |
| Challenger Nur-Sultan | 2021/07/21 06:30 | Nick Chappell v Sergiy Stakhovsky | 7-6,6-4 |
| Challenger Nur-Sultan | 2021/07/19 07:05 | Grigoriy Lomakin v Nick Chappell | 3-6,6-7 |
| Challenger Nur-Sultan | 2021/07/12 08:45 | Beibit Zhukayev v Nick Chappell | 4-6,6-3,7-6 |
| ITF M25 Nur-Sultan | 2021/07/07 05:10 | Sanjar Fayziev v Nick Chappell | 6-4,6-4 |
| ITF M25 Bakio | 2021/06/30 10:00 | Antoine Bellier v Nick Chappell | 3-6,6-4,6-4 |
| ATP Eastbourne | 2021/06/19 15:45 | Nick Chappell v Mikhail Kukushkin | 2-6,3-6 |
| 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 |
| ITF M25 Santo Domingo | 2021/06/04 14:25 | Calvin Hemery v Roy Smith | 4-6,2-6 |
| ITF M25 Santo Domingo | 2021/06/03 16:45 | Roy Smith v Yshai Oliel | 4-6,6-2,6-3 |
| ITF M25 Santo Domingo | 2021/06/03 13:00 | Roy Smith v Maxime Mora | 6-0,6-0 |
| ITF M15 Monastir | 2021/05/28 08:30 | Eliakim Coulibaly v Roy Smith | 6-3,6-4 |