Stadium: Court 14 Round: 27 Ground: Clay
| ITF M15 Eindhoven | 2023/08/02 15:40 | Matyas Fuele v Jip Van Assendelft | 4-6,3-6 |
| ITF M15 Eindhoven | 2023/08/01 16:30 | Jack Loge v Jip Van Assendelft | 6-4,4-6,1-6 |
| ITF M15 Eindhoven | 2023/07/31 10:30 | Jip Van Assendelft v Alen Moritz Hodzic | 6-2,6-3 |
| ITF M15 Eindhoven | 2023/07/30 07:00 | Ethan Cook v Jip Van Assendelft | 6-4,3-6,4-10 |
| ITF M25 Arlon | 2023/06/27 09:30 | Charlelie Cosnet v Jip Van Assendelft | 7-6,6-3 |
| ITF M25 Arlon | 2023/06/26 14:55 | Alex Degabriele v Jip Van Assendelft | 3-6,4-6 |
| UTR Pro Hilversum | 2023/06/11 07:30 | Twan Van Zijl v Jip Van Assendelft | 4-6,4-5 |
| UTR Pro Hilversum | 2023/06/10 06:00 | Mats Bredschneijder v Jip Van Assendelft | 6-4,0-6,1-6 |
| ITF M15 Eindhoven | 2023/08/02 08:45 | Stijn Paardekooper v Maxime Mora | 3-6,6-4,6-2 |
| ITF M15 Eindhoven | 2023/08/01 12:20 | Paul Barbier Gazeu v Stijn Paardekooper | 3-6,4-6 |
| ITF M15 Eindhoven | 2023/07/31 08:00 | Stijn Paardekooper v Rik Muller | 6-2,6-2 |
| ITF M15 Eindhoven | 2023/07/30 10:30 | Elgin Khoeblal v Stijn Paardekooper | 4-6,6-2,8-10 |
| ITF M25 Haag | 2023/07/03 10:00 | Jakub Wojcik v Stijn Paardekooper | 6-4,6-2 |
| ITF M25 Haag | 2023/07/02 10:30 | Stijn Paardekooper v Lodewijk Weststrate | 6-2,6-4 |
| ITF M15 Alkmaar | 2023/06/25 10:00 | Guy Den Heijer v Stijn Paardekooper | 4-6,6-4,12-14 |