Stadium: Grandstand Round: 14 Ground: Hardcourt outdoor
| Challenger Barcelona | 2021/10/03 08:00 | Georgii Kravchenko v Vladyslav Orlov | 6-4,6-1 |
| ITF M15 Antalya | 2020/12/26 07:45 | Vladyslav Orlov v Georgii Kravchenko | 1-6,2-6 |
| ITF M15 Antalya | 2020/12/20 07:30 | Georgii Kravchenko v Vladyslav Orlov | 6-2,3-6,4-6 |
| ITF M25 Portimao | 2021/10/29 09:30 | Vladyslav Orlov v Maximilian Neuchrist | 3-6,3-6 |
| ITF M25 Portimao | 2021/10/28 11:35 | Vladyslav Orlov v Goncalo Falcao | 6-3,6-3 |
| ITF M25 Portimao | 2021/10/27 11:20 | Vladyslav Orlov v Tiago Cacao | 6-3,6-1 |
| ITF M25 Hamburg | 2021/10/21 08:00 | Daniel Little v Vladyslav Orlov | 7-5,6-1 |
| ITF M25 Hamburg | 2021/10/19 10:55 | Tom Schonenberg v Vladyslav Orlov | 3-6,6-7 |
| Challenger Alicante | 2021/10/11 14:30 | Vladyslav Orlov v Mischa Zverev | 2-6,1-6 |
| Challenger Barcelona | 2021/10/03 08:00 | Georgii Kravchenko v Vladyslav Orlov | 6-4,6-1 |
| Challenger Bucharest | 2021/09/19 11:35 | Dragos Nicolae Madaras v Vladyslav Orlov | 3-6,6-1,6-0 |
| Challenger Losinj | 2021/10/21 10:40 | Nerman Fatic v Georgii Kravchenko | 6-3,2-6,6-3 |
| Challenger Losinj | 2021/10/19 11:45 | Georgii Kravchenko v Blaz Rola | 6-4,6-2 |
| Challenger Losinj | 2021/10/18 08:00 | Georgii Kravchenko v Anirudh Chandrasekar | 6-0,6-1 |
| Challenger Losinj | 2021/10/17 09:25 | Georgii Kravchenko v Gal Emersic Potocnik | 6-2,6-2 |
| Challenger Alicante | 2021/10/12 11:40 | Georgii Kravchenko v Mario Vilella Martinez | 3-6,2-6 |
| Challenger Alicante | 2021/10/11 09:00 | Robert Galloway v Georgii Kravchenko | 6-4,1-6,2-6 |
| Challenger Alicante | 2021/10/10 09:35 | Luis Patino v Georgii Kravchenko | 2-6,1-6 |
| Challenger Barcelona | 2021/10/05 11:20 | Georgii Kravchenko v Damir Dzumhur | 6-3,3-6,1-6 |