Stadium: Court 14 Round: 44 Ground: Hardcourt outdoor
| ITF - Heraklion M15 | 2023/10/16 06:30 | Graham Maassen v Ki Lung NG | 2-6,4-6 |
| ITF - Heraklion M15 | 2023/10/15 07:00 | Stefan Cizelj-Zivkovic v Graham Maassen | 3-6,3-6 |
| ITF - Lakewood M15 | 2023/07/03 17:00 | Dominique Rolland v Graham Maassen | 6-4,6-2 |
| ITF - South Bend M15 | 2023/06/19 14:00 | Muzammil Murtaza v Graham Maassen | 7-6,7-5 |
| ITF - Tabasco M15 | 2023/05/23 19:30 | Christopher Bulus v Graham Maassen | 6-0,6-2 |
| ITF - Tabasco M15 | 2023/05/22 16:00 | Alexey Shtengelov v Graham Maassen | 3-6,3-6 |
| ITF - Tabasco M15 | 2023/05/21 19:00 | Ricardo Reyna v Graham Maassen | 2-6,6-3,6-10 |
| ITF - Xalapa M25 | 2023/05/15 19:30 | Juan Sebastian Osorio v Graham Maassen | 6-0,6-3 |
| ITF - Vejle M15 | 2023/07/24 12:00 | Andrea Gola v Ivan Sergeyev | 7-5,6-4 |
| ITF - Vejle M15 | 2023/07/24 07:00 | Gustav Theilgaard v Ivan Sergeyev | 4-6,4-6 |
| ITF - Kamen M15 | 2023/06/26 10:00 | Aloys J W Van Baal v Ivan Sergeyev | 6-3,6-2 |
| UTR Pro - Hilversum | 2023/06/10 07:30 | Sander Jong v Ivan Sergeyev | 6-2,6-0 |
| UTR Pro - Hilversum | 2023/06/09 06:00 | Ivan Sergeyev v Victor Sklenka | 6-4,6-7,6-0 |
| UTR Pro - Hilversum | 2023/06/07 07:30 | Ivan Sergeyev v Julian Cundom | 6-3,6-2 |
| UTR Pro - Hilversum | 2023/06/06 06:00 | Ivan Sergeyev v Quentin Robert | 4-6,2-5 |
| UTR Pro - Hilversum | 2023/06/05 07:30 | Guy Den Heijer v Ivan Sergeyev | 0-6,2-6 |