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 |
| ITF M25 Prague | 2021/10/07 13:00 | Timo Stodder v Vasil Kirkov | 6-2,6-1 |
| ITF M25 Prague | 2021/10/06 07:55 | Vasil Kirkov v Adam Januska | 6-0,6-0 |
| ITF M25 Falun | 2021/10/01 14:30 | Vasil Kirkov v Shintaro Imai | 2-6,5-7 |
| ITF M25 Falun | 2021/09/30 14:20 | Antoine Escoffier v Vasil Kirkov | 6-3,4-6,4-6 |
| ITF M25 Falun | 2021/09/29 15:20 | Vasil Kirkov v Leopold Zima | 6-4,6-4 |
| ITF M25 Falun | 2021/09/27 12:00 | Sergey Fomin v Vasil Kirkov | 3-6,2-6 |
| ITF M25 Plaisir | 2021/09/17 11:30 | Thomas Laurent v Vasil Kirkov | 6-7,1-6 |
| ITF M25 Plaisir | 2021/09/16 07:55 | Vasil Kirkov v Marvin Moeller | 2-6,7-6,7-6 |
| 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 |
| Challenger Mallorca | 2021/09/01 14:00 | Nick Chappell v Evgeny Karlovskiy | 6-3,6-1 |