Stadium: Hard Court 3 Round: 62 Ground: Hardcourt outdoor
| ITF - M25 Heraklion | 2023/11/06 07:00 | Graham Maassen v Simon Freund | 4-6,2-6 |
| 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 |
| ITF - M15 Heraklion | 2023/10/24 06:30 | Graham Maassen v Alessandro Spadola | 6-4,6-2 |
| ITF - M15 Heraklion | 2023/10/23 07:30 | Eero Vasa v Graham Maassen | 4-6,6-3,7-10 |
| 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 |
| 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 |