Stadium: Court 16 Round: 26 Ground: Hardcourt outdoor
| ITF M15 Heraklion | 2023/10/25 08:30 | Jonas Trinker v Stefan Palosi | 6-3,7-5 |
| ITF M15 Heraklion | 2023/10/24 06:30 | Jonas Trinker v Alexander Orlov | 6-3,6-1 |
| ITF M15 Heraklion | 2023/10/23 09:00 | Jonas Trinker v Gianluca Carlini | 6-3,6-4 |
| ITF M15 Heraklion | 2023/10/18 09:50 | Alexandros Skorilas v Jonas Trinker | 6-2,7-6 |
| ITF M25 Falun | 2023/09/27 11:55 | Jonas Trinker v Evgeny Karlovskiy | 2-6,2-6 |
| ITF M25 Falun | 2023/09/26 13:35 | Sebastian Eriksson v Jonas Trinker | 6-2,3-6,4-6 |
| ITF M25 Falun | 2023/09/25 07:55 | Jonas Trinker v Simon Freund | 5-7,6-1,10-2 |
| ITF M25 Falun | 2023/09/24 09:15 | Jonas Trinker v Alfons Ridstrom | 6-2,6-2 |
| Challenger Olbia | 2023/10/17 16:10 | 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 M25 Zlatibor | 2023/09/29 13:30 | Marko Topo v Vladyslav Orlov | 6-1,6-2 |
| ITF M25 Zlatibor | 2023/09/29 09:50 | Jaka Protic Zakelj v Vladyslav Orlov | 2-6,1-6 |
| ITF M25 Zlatibor | 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 |