Stadium: Court 2 Round: 14 Ground: Clay
| Challenger Ostrava | 2021/04/28 09:00 | Elias Ymer v Sergiy Stakhovsky | 6-1,6-2 |
| Challenger Ostrava | 2021/04/27 09:10 | Patrik Rikl v Sergiy Stakhovsky | 4-6,2-6 |
| Challenger Rome | 2021/04/22 09:00 | Lorenzo Giustino v Sergiy Stakhovsky | 6-4,6-4 |
| Challenger Rome | 2021/04/20 11:40 | Sergiy Stakhovsky v Mathias Bourgue | 6-4,3-6,7-5 |
| Challenger Lugano | 2021/03/25 11:00 | Sergiy Stakhovsky v Vitaliy Sachko | 3-6,1-6 |
| Challenger Lugano | 2021/03/23 11:25 | Sergiy Stakhovsky v Francesco Forti | 6-4,6-2 |
| Challenger Biella | 2021/03/19 13:05 | Daniel Masur v Sergiy Stakhovsky | 7-6,6-4 |
| Challenger Biella | 2021/03/17 13:35 | Sergiy Stakhovsky v Marc-Andrea Huesler | 7-5,3-6,7-6 |