Stadium: Center Court Round: 26 Ground: Hardcourt outdoor
| 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 - Nur-Sultan M25 | 2021/07/07 05:10 | Sanjar Fayziev v Nick Chappell | 6-4,6-4 |
| ITF - Bakio M25 | 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 |
| Challenger Aix en Provence | 2021/06/13 08:30 | Nick Chappell v Sadio Doumbia | 0-6,4-6 |
| Challenger Orlando | 2021/06/07 14:00 | Thiago Agustin Tirante v Nick Chappell | 6-3,6-4 |
| Challenger Orlando | 2021/06/06 14:00 | Ryan Harrison v Nick Chappell | 2-6,6-7 |
| Challenger Nur-Sultan | 2021/07/20 07:20 | Benjamin Lock v Sergiy Stakhovsky | 3-6,6-3,5-7 |
| Challenger Nur-Sultan | 2021/07/15 06:00 | Sergiy Stakhovsky v Jason Kubler | 2-6,6-3,2-6 |
| Challenger Nur-Sultan | 2021/07/13 06:10 | Sergiy Stakhovsky v Pavel Kotov | 7-5,6-2 |
| Challenger Porto | 2021/07/03 10:00 | Altug Celikbilek v Sergiy Stakhovsky | 6-2,6-1 |
| Challenger Porto | 2021/07/02 12:00 | Goncalo Oliveira v Sergiy Stakhovsky | 6-7,6-7 |
| Challenger Porto | 2021/06/30 13:45 | Matteo Viola v Sergiy Stakhovsky | 2-6,6-4,5-7 |
| Challenger Porto | 2021/06/28 14:50 | Sergiy Stakhovsky v Go Soeda | 2-6,6-2,7-6 |
| Wimbledon | 2021/06/23 14:15 | Gregoire Barrere v Sergiy Stakhovsky | 7-5,6-3 |