Stadium: Court 15 Round: 25 Ground: Hardcourt outdoor
| ITF - Heraklion M15 | 2023/10/21 07:00 | Jakub Nicod v Oliver Ojakaar | 6-4,4-6,6-4 |
| ITF - Heraklion M15 | 2023/10/20 07:00 | Oleg Prihodko v Oliver Ojakaar | 1-6,7-5,2-6 |
| ITF - Heraklion M15 | 2023/10/19 06:30 | Oliver Ojakaar v Szymon Kielan | 7-6,7-6 |
| ITF - Heraklion M15 | 2023/10/18 06:30 | David Quayle v Oliver Ojakaar | 3-6,3-6 |
| ITF - Falun M25 | 2023/09/25 07:50 | Johannes Ingildsen v Oliver Ojakaar | 6-2,6-2 |
| ITF - Falun M25 | 2023/09/24 08:00 | Filip Stidell v Oliver Ojakaar | 1-6,2-6 |
| ITF - Danderyd M15 | 2023/09/20 12:25 | Oliver Ojakaar v Mats Rosenkranz | 4-6,6-4,3-6 |
| ITF - Krsko M15 | 2023/05/19 11:30 | Lucas Gerch v Oliver Ojakaar | 1-6,6-3,6-4 |
| 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 |
| Challenger Sibiu | 2023/09/17 08:55 | Kai Wehnelt v Vladyslav Orlov | 7-5,6-7,6-4 |