Stadium: Center Court Round: 62 Ground: Hardcourt outdoor
| ITF M25 Heraklion | 2023/11/27 10:00 | Stephanos Schinas v Maximo Nagele | 7-5,6-3 |
| ITF M15 Heraklion | 2023/11/20 11:00 | Gorazd Srbljak v Stephanos Schinas | 7-5,6-3 |
| ITF M25 Heraklion | 2023/11/12 12:00 | Lior Goldenberg v Stephanos Schinas | 6-0,6-4 |
| ITF M25 Heraklion | 2023/11/06 09:00 | Younes Lalami Laaroussi v Stephanos Schinas | 6-3,6-1 |
| ITF M25 Heraklion | 2023/10/30 09:30 | Stephanos Schinas v Ki Lung NG | 7-6,3-6,8-10 |
| ITF M25 Heraklion | 2023/10/29 10:00 | Stephanos Schinas v Thomas Sorensen | 3-6,7-6,10-7 |
| ITF M15 Heraklion | 2023/10/25 12:05 | Stephanos Schinas v Gabriel Decamps | 2-6,3-6 |
| ITF M15 Heraklion | 2023/10/17 06:30 | Benoit Torcq v Stephanos Schinas | 6-7,6-4,10-3 |
| ITF M15 Heraklion | 2023/11/21 07:00 | Graham Maassen v Neil Oberleitner | 2-6,2-6 |
| ITF M25 Heraklion | 2023/11/13 08:30 | Graham Maassen v Simon Freund | 3-6,2-6 |
| ITF M25 Heraklion | 2023/11/12 07:00 | Christos Antonopoulos v Graham Maassen | 4-6,4-6 |
| 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 | Graham Maassen v Mihail Ivanov | 6-2,6-4 |
| ITF M25 Heraklion | 2023/10/30 07:00 | Yan Sabanin v Graham Maassen | 6-4,6-4 |
| ITF M25 Heraklion | 2023/10/29 09:00 | Glauco Pinheiro Da Cruz Junior v Graham Maassen | 6-2,2-6,12-14 |
| ITF M15 Heraklion | 2023/10/25 08:10 | Adam Heinonen v Graham Maassen | 6-4,6-3 |