Stadion: Hard 21 Round: 25 Ground: Hardcourt outdoor
| ITF - M15 - Heraklion | 2023/11/21 07:00 | Jannik Maute v Kevin Humpfner | 6-3,7-5 |
| ITF - M15 - Heraklion | 2023/11/20 10:00 | Jannik Maute v Max Benaim | 6-4,6-2 |
| ITF - M15 - Heraklion | 2023/11/19 09:00 | Jannik Maute v Ben Chetewy Ungar | 6-1,6-2 |
| ITF - M15 - Heraklion | 2023/11/15 10:50 | Jannik Maute v Alex Knaff | 3-6,3-6 |
| ITF - M25 - Heraklion | 2023/11/14 07:30 | Jannik Maute v Arthur Van Der Kooij | 6-4,6-4 |
| ITF - M25 - Heraklion | 2023/11/13 13:45 | Jannik Maute v Sergo Sikharulidze | 6-2,6-1 |
| ITF - M25 - Heraklion | 2023/11/12 12:00 | Jannik Maute v Filip Krolo | 6-1,7-5 |
| ITF - M15 - Al Zahra | 2023/11/01 07:00 | Jannik Maute v Niklas Schell | 3-6,4-6 |
| ITF - M15 - Heraklion | 2023/11/21 07:00 | Lars Goran Verwerft v Simon Freund | 6-1,5-7,8-10 |
| ITF - M15 - Heraklion | 2023/11/20 13:45 | Adrian Arcon v Simon Freund | 2-6,0-6 |
| ITF - M15 - Heraklion | 2023/11/19 15:30 | Vincent Jonah Strauch v Simon Freund | 3-6,3-6 |
| ITF - M25 - Heraklion | 2023/11/14 07:30 | James Davis v Simon Freund | 6-4,5-7,10-7 |
| ITF - M25 - Heraklion | 2023/11/13 08:30 | Graham Maassen v Simon Freund | 3-6,2-6 |
| ITF - M25 - Heraklion | 2023/11/07 07:30 | Guy Den Heijer v Simon Freund | 6-2,3-6,10-5 |
| 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 |