Stadium: Center Court Round: 62 Ground: Hardcourt outdoor
| 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 - M15 Heraklion | 2023/10/23 10:30 | Guy Den Heijer v Vojtech Mares | 5-7,7-6,10-6 |
| ITF - M25 Heraklion | 2023/11/05 07:00 | Evangelos Kypriotis v Jacques-Kai Inoue | 6-4,6-1 |
| ITF - M25 Heraklion | 2023/10/30 07:00 | Benjamin Pietri v Evangelos Kypriotis | 6-1,6-4 |
| ITF - M25 Heraklion | 2023/10/29 07:00 | Evangelos Kypriotis v Qing Lihao | 6-0,6-2 |
| ITF - M15 Heraklion | 2023/10/15 08:30 | Evangelos Kypriotis v Thomas Kostka | 2-6,1-6 |
| ITF - M15 Monastir | 2023/07/23 15:00 | Dusan Rsovac v Evangelos Kypriotis | 7-5,7-6 |
| ITF - M15 Monastir | 2023/07/09 08:30 | Evangelos Kypriotis v Max Batyutenko | 5-7,4-6 |
| ITF - M15 Monastir | 2023/07/03 08:30 | Evangelos Kypriotis v Ewan Moore | 2-6,2-6 |
| ITF - M15 Monastir | 2023/07/02 08:30 | Evangelos Kypriotis v Guilherme Meale | 6-4,7-5 |