Stadium: Centre Court Round: 28 Ground: Clay
| ITF M15 Alkmaar | 2023/06/30 14:30 | Alec Deckers v Luke Simkiss | 6-7,6-4,4-6 |
| ITF M15 Alkmaar | 2023/06/29 10:55 | Luke Simkiss v Sidane Pontjodikromo | 6-3,7-5 |
| ITF M15 Alkmaar | 2023/06/28 13:55 | Luke Simkiss v Florian Broska | 6-7,6-4,7-6 |
| ITF M15 Alkmaar | 2023/06/25 10:00 | Luke Tollenaar v Luke Simkiss | 0-6,1-6 |
| UTR Pro London | 2023/05/20 08:30 | Weightman, Oscar v Luke Simkiss | 6-3,6-0 |
| UTR Pro London | 2023/05/19 10:40 | Luke Simkiss v Stefan Cooper | 6-7,4-6 |
| UTR Pro London | 2023/05/17 07:00 | Luke Simkiss v Ivan Denisov | 2-6,7-5,6-4 |
| UTR Pro London | 2023/05/16 08:30 | Luke Simkiss v Sklenka, Victor | 6-7,7-6,7-6 |
| ITF M15 Alkmaar | 2023/06/30 12:05 | Ryan Nijboer v Sander Jong | 3-6,4-6 |
| ITF M15 Alkmaar | 2023/06/27 11:10 | Sander Jong v Matthew Dellavedova | 6-4,6-2 |
| Saarlouis, Singles Qualifying M-ITF-GER-07A | 2023/06/25 12:00 | Sander Jong v von Der Schulenburg, Jeffrey | 6-1,6-0 |
| Saarlouis, Singles Qualifying M-ITF-GER-07A | 2023/06/24 11:00 | Joao Fonseca v Sander Jong | 4-6,3-6 |
| Saarlouis, Singles Qualifying M-ITF-GER-07A | 2023/06/23 12:30 | Lodewijk Weststrate v Sander Jong | 3-6,7-5,2-6 |
| Saarlouis, Singles Qualifying M-ITF-GER-07A | 2023/06/22 12:30 | Sander Jong v Alex Knaff | 6-4,6-3 |
| Saarlouis, Singles Qualifying M-ITF-GER-07A | 2023/06/20 11:35 | Yannik Kelm v Sander Jong | 1-6,0-6 |
| ITF M15 Duffel | 2023/06/15 10:00 | Jahn, Jeremy v Sander Jong | 7-6,6-4 |