Stadium: Campo 2 Round: 19 Ground: Hardcourt outdoor
| Challenger Olbia | 2023/10/15 08:00 | Maks Kasnikowski v N. Vijay Sundar Prashanth | 6-3,6-4 |
| Challenger Mouilleron le Captif | 2023/10/01 16:00 | Maks Kasnikowski v Evgeny Karlovskiy | 6-7,7-6,4-6 |
| Challenger Bad Waltersdorf | 2023/09/19 08:00 | Maks Kasnikowski v Francesco Passaro | 6-0,5-7,1-6 |
| Challenger Bad Waltersdorf | 2023/09/18 09:25 | Maks Kasnikowski v Petr Nouza | 6-3,3-6,3-6 |
| Challenger Bad Waltersdorf | 2023/09/17 12:30 | Maks Kasnikowski v Syl Gaxherri | 6-1,7-5 |
| Challenger Szczecin | 2023/09/14 13:45 | Maks Kasnikowski v Jaume Munar | 4-6,3-6 |
| Challenger Tulln | 2023/09/04 08:00 | Maks Kasnikowski v Jeremy Jahn | 1-6,4-6 |
| Challenger Tulln | 2023/09/03 08:00 | Maks Kasnikowski v Paul Werren | 6-1,6-3 |
| Challenger Olbia | 2023/10/15 08:00 | Arjun Kadhe v Vladyslav Orlov | 0-6,3-6 |
| Challenger Alicante | 2023/10/01 13:05 | Lukas Pokorny v Vladyslav Orlov | 6-3,6-0 |
| ITF - Zlatibor M25 | 2023/09/29 13:30 | Marko Topo v Vladyslav Orlov | 6-1,6-2 |
| ITF - Zlatibor M25 | 2023/09/29 09:50 | Jaka Protic Zakelj v Vladyslav Orlov | 2-6,1-6 |
| ITF - Zlatibor M25 | 2023/09/28 12:55 | Shayan Najam v Vladyslav Orlov | 0-6,0-6 |
| Challenger Sibiu | 2023/09/17 08:55 | Kai Wehnelt v Vladyslav Orlov | 7-5,6-7,6-4 |
| Puchar Davisa | 2023/09/15 10:50 | Vladyslav Orlov v Nicolas Mejia | 5-7,6-4,7-6 |
| Puchar Davisa | 2023/09/14 09:50 | Vladyslav Orlov v Daniel Elahi Galan | 7-5,3-6,0-6 |