Stadium: Hard 20 Round: 25 Ground: Hardcourt outdoor
| 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 |
| ITF M15 Heraklion | 2023/10/24 06:30 | Graham Maassen v Alessandro Spadola | 6-4,6-2 |
| ITF M15 Heraklion | 2023/11/16 11:05 | Neil Oberleitner v Sean Hodkin | 1-6,4-6 |
| ITF M15 Heraklion | 2023/11/14 08:30 | Neil Oberleitner v Petros Chrysochos | 6-2,6-4 |
| ITF M25 Trnava | 2023/11/07 15:30 | Neil Oberleitner v Leo Borg | 4-6,4-6 |
| Challenger Ismaning | 2023/10/30 10:00 | Joao Sousa v Neil Oberleitner | 7-6,6-3 |
| Challenger Ismaning | 2023/10/29 09:30 | Neil Oberleitner v Leo Borg | 6-1,6-4 |
| ITF M25 Edgbaston | 2023/10/17 08:55 | Connor Thomson v Neil Oberleitner | 6-3,7-6 |
| ITF M25 Rodez | 2023/10/12 14:45 | Hady Habib v Neil Oberleitner | 7-6,4-6,7-6 |
| ITF M25 Rodez | 2023/10/11 11:55 | Neil Oberleitner v Federico Bertuccioli | 6-2,6-4 |