Stadium: Hard 17 Round: 27 Ground: Hardcourt outdoor
| ITF M25 Heraklion | 2023/11/02 10:00 | Guy Den Ouden v Szymon Kielan | 7-5,6-0 |
| ITF M25 Heraklion | 2023/11/01 11:55 | Guy Den Ouden v Benjamin Pietri | 2-6,6-3,6-2 |
| ITF M15 Heraklion | 2023/10/27 07:00 | Guy Den Ouden v Adam Heinonen | 6-7,6-1,2-6 |
| ITF M15 Heraklion | 2023/10/25 06:30 | Guy Den Ouden v Ioannis Kountourakis | 7-5,6-4 |
| ITF M15 Heraklion | 2023/10/20 07:00 | Guy Den Ouden v Jakub Nicod | 2-6,6-7 |
| ITF M15 Heraklion | 2023/10/19 08:45 | Dax Donders v Guy Den Ouden | 6-7,5-7 |
| ITF M15 Heraklion | 2023/10/18 07:25 | Guy Den Ouden v Matthew William Donald | 6-4,6-2 |
| ITF M15 Heraklion | 2023/10/17 06:30 | Guy Den Ouden v David Quayle | 6-1,7-5 |
| ITF M25 Heraklion | 2023/11/02 08:00 | Vladyslav Orlov v Francesco Forti | 6-1,6-1 |
| ITF M25 Heraklion | 2023/11/01 08:35 | Vladyslav Orlov v Dax Donders | 6-1,6-4 |
| ITF M15 Heraklion | 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 M25 Zlatibor | 2023/09/29 13:30 | Marko Topo v Vladyslav Orlov | 6-1,6-2 |