Stadium: Court 5 Round: 26 Ground: Hardcourt indoor
| ITF M15 Cancun | 2019/12/15 15:00 | Nick Chappell v Vasil Kirkov | 7-6,6-7,6-7 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/17 07:00 | Vasil Kirkov v Adriano Dzhenev | 6-3,6-2 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/16 06:00 | Vasil Kirkov v Yanaki Milev | 6-1,6-1 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/14 07:30 | Vasil Kirkov v Aleksandr Braynin | 7-5,5-1 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/13 10:30 | Vasil Kirkov v Gorazd Srbljak | 2-6,6-3,1-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/12 06:00 | Vladimir Popov v Vasil Kirkov | 2-6,4-6 |
| ITF M15 Sofia | 2021/07/06 11:05 | Francisco Comesana v Vasil Kirkov | 6-3,6-2 |
| ITF M15 Champaign | 2021/06/23 19:10 | Vasil Kirkov v Kyle Seelig | 6-4,3-6,6-7 |
| ITF M25 Tulsa | 2021/06/15 14:00 | Vasil Kirkov v Michael Shabaz | 3-6,6-1,7-10 |
| 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 |
| 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 Little Rock | 2021/06/02 16:30 | Dayne Kelly v Nick Chappell | 6-1,7-5 |