Stadium: Court 15 Round: 25 Ground: Hardcourt outdoor
| ITF - Heraklion M15 | 2023/10/26 06:30 | Jonas Trinker v Vladyslav Orlov | 6-4,1-6,6-2 |
| Challenger Olbia | 2023/10/18 09:45 | Vladyslav Orlov v Kyrian Jacquet | 7-5,3-6,4-6 |
| Challenger Olbia | 2023/10/16 08:00 | Maks Kasnikowski v Vladyslav Orlov | 6-4,6-7,4-6 |
| 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 |
| ITF - Heraklion M25 | 2023/10/31 07:00 | Dax Donders v Ki Lung NG | 6-2,6-2 |
| ITF - Heraklion M25 | 2023/10/30 09:30 | Dax Donders v Dario Drebenstedt | 6-1,6-2 |
| ITF - Heraklion M15 | 2023/10/25 06:30 | Valentin Royer v Dax Donders | 6-3,6-4 |
| ITF - Heraklion M15 | 2023/10/24 06:30 | Dax Donders v Louis Dussin | 5-7,4-6 |
| ITF - Heraklion M15 | 2023/10/23 09:00 | Dax Donders v Hamid Reza Nadaf | 7-6,6-2 |
| ITF - Heraklion M15 | 2023/10/19 08:45 | Dax Donders v Guy Den Ouden | 6-7,5-7 |
| ITF - Heraklion M15 | 2023/10/17 09:00 | Stefanos Sakellaridis v Dax Donders | 4-6,1-6 |
| ITF - Santa Margherita M25 | 2023/09/26 08:00 | Dax Donders v Daniel Michalski | 3-6,3-6 |