Stadium: Hard 20 Round: 62 Ground: Hardcourt outdoor
| ITF M25 Heraklion | 2023/11/06 07:00 | Guy Den Heijer v Evangelos Kypriotis | 6-1,7-5 |
| ITF M25 Heraklion | 2023/11/03 10:20 | Guy Den Heijer v Enrico Dalla Valle | 2-6,1-6 |
| ITF M25 Heraklion | 2023/11/02 08:00 | Guy Den Heijer v Marlon Vankan | 6-3,7-5 |
| ITF M25 Heraklion | 2023/11/01 12:00 | Stefanos Sakellaridis v Guy Den Heijer | 7-5,3-6,6-7 |
| ITF M25 Heraklion | 2023/10/31 07:00 | Guy Den Heijer v Joshua Charlton | 6-4,7-5 |
| ITF M25 Heraklion | 2023/10/30 09:30 | Guy Den Heijer v Gabriel Matuszewski | 6-1,6-4 |
| ITF M15 Heraklion | 2023/10/25 08:55 | Mario G Fernandez v Guy Den Heijer | 6-1,6-3 |
| ITF M15 Heraklion | 2023/10/24 06:30 | Guy Den Heijer v Joshua Charlton | 7-6,7-5 |
| ITF M25 Heraklion | 2023/11/06 07:00 | Graham Maassen v Simon Freund | 4-6,2-6 |
| ITF M25 Heraklion | 2023/11/05 07:00 | Simon Freund v Filippo Romano | 6-2,6-1 |
| ITF M25 Tavira | 2023/10/17 10:30 | Diego F Flores v Simon Freund | 6-1,6-4 |
| ITF M25 Tavira | 2023/10/16 08:30 | Simon Freund v Tomas Vaise | 6-3,6-2 |
| ITF M25 Tavira | 2023/10/15 09:00 | Jasin Jakupi v Simon Freund | 2-6,1-6 |
| ITF M25 Tavira | 2023/10/12 09:00 | Aleksandr Braynin v Simon Freund | 6-4,6-4 |
| ITF M25 Tavira | 2023/10/11 08:30 | Simon Freund v Diogo Marques | 6-3,7-6 |
| ITF M25 Tavira | 2023/10/10 08:30 | Alexis Boureau v Simon Freund | 3-6,1-6 |