Stadium: Centre Court Round: 14 Ground: Clay
| Challenger Maia | 2021/12/14 14:35 | Oleksii Krutykh v Gastao Elias | 6-4,2-6,5-7 |
| Challenger Antalya | 2021/12/08 11:15 | Nick Hardt v Oleksii Krutykh | 7-5,6-3 |
| ITF M25 Nur-Sultan | 2021/10/27 09:50 | Mikalai Haliak v Oleksii Krutykh | 7-6,6-4 |
| ITF M25 Nur-Sultan | 2021/10/21 07:05 | Oleksii Krutykh v Grigoriy Lomakin | 6-4,6-7,3-6 |
| ITF M25 Nur-Sultan | 2021/10/20 09:50 | Oleksii Krutykh v Jonathan Baron | 6-2,6-3 |
| Challenger Barcelona | 2021/10/07 10:40 | Hugo Gaston v Oleksii Krutykh | 6-0,6-2 |
| Challenger Barcelona | 2021/10/05 14:30 | Oleksii Krutykh v Pablo Llamas Ruiz | 6-2,6-2 |
| Challenger Barcelona | 2021/10/04 13:00 | Oleksii Krutykh v Yshai Oliel | 1-6,2-6 |
| ITF M15 Ostrava | 2021/11/24 14:25 | Matthew William Donald v Jiri Barnat | 3-6,6-7 |
| ITF M15 Opava | 2021/11/17 10:40 | Matthew William Donald v Henri Squire | 2-6,6-7 |
| ITF M15 Parnu | 2021/10/27 12:05 | Oscar Moraing v Matthew William Donald | 7-5,6-1 |
| ITF M25 Prague | 2021/10/06 12:20 | Tobias Simon v Matthew William Donald | 6-3,4-6,6-3 |
| ITF M25 Pardubice | 2021/09/23 11:15 | Matthew William Donald v Luca Nardi | 4-6,3-6 |
| ITF M25 Pardubice | 2021/09/22 09:00 | Tomas Lanik v Matthew William Donald | 2-6,2-6 |
| ITF M25 Prostejov | 2021/08/16 11:15 | Zsombor Piros v Matthew William Donald | 6-3,6-4 |
| Challenger Liberec | 2021/08/01 14:00 | Matthew William Donald v Rudolf Molleker | 6-4,5-7,5-7 |