Stadium: Court 2 Round: 14 Ground: Hardcourt outdoor
| 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 | Kamke, Tobias v Nick Chappell | 6-2,6-4 |
| Challenger Mallorca | 2021/09/01 14:00 | Nick Chappell v Evgeny Karlovskiy | 6-3,6-1 |
| Challenger Mallorca | 2021/08/31 08:00 | Rafael Giotis v Nick Chappell | 3-6,4-6 |
| Challenger Mallorca | 2021/08/30 08:00 | Joan Nadal v Nick Chappell | 1-6,2-6 |
| Challenger - Prague | 2021/08/23 10:00 | Kaichi Uchida v Nick Chappell | 6-4,3-6,6-1 |
| Prostejov, Singles M-ITF-CZE-04A | 2021/08/19 08:15 | Alex Rybakov v Nick Chappell | 6-2,7-6 |
| Prostejov, Singles M-ITF-CZE-04A | 2021/08/18 10:30 | Daniel Paty v Nick Chappell | 4-6,3-6 |
| Challenger Kyiv | 2021/09/06 08:00 | Kalenichenko, Danylo v Ivan Gakhov | 4-6,2-6 |
| Challenger Kyiv | 2021/09/05 09:25 | Otto Virtanen v Kalenichenko, Danylo | 6-3,2-6,4-6 |
| ITF M15 Bratislava | 2021/08/29 08:00 | Mate Valkusz v Kalenichenko, Danylo | 6-0,6-2 |
| ITF M15 Bratislava | 2021/08/28 09:00 | Nejedly, Pavel v Kalenichenko, Danylo | 4-6,2-6 |
| ITF M15 Bratislava | 2021/08/27 09:50 | Stefan Palosi v Kalenichenko, Danylo | 4-6,5-7 |
| ITF M15 Bratislava | 2021/08/26 08:00 | Gorazd Srbljak v Kalenichenko, Danylo | 6-7,0-6 |
| ITF M15 Bratislava | 2021/08/25 08:00 | Lukas Palovic v Kalenichenko, Danylo | 2-6,2-6 |
| ITF M15 Bratislava | 2021/08/17 10:30 | Peter Fajta v Kalenichenko, Danylo | 4-6,6-3,6-2 |