Stadium: Court 3 Round: 27 Ground: Hardcourt outdoor
| ITF - M15 Monastir | 2023/09/14 08:30 | Samir Hamza Reguig v Oscar Weightman | 1-6,4-6 |
| ITF - M15 Monastir | 2023/09/13 08:30 | Oscar Weightman v Matteo Covato | 6-3,6-2 |
| ITF - M15 Monastir | 2023/09/07 08:00 | Karue Sell v Oscar Weightman | 6-4,6-3 |
| ITF - M15 Monastir | 2023/09/06 10:00 | Oscar Weightman v Alexandros Skorilas | 6-2,4-6,6-4 |
| ITF - M25 Aldershot | 2023/08/17 10:15 | Henry Searle v Oscar Weightman | 6-3,6-2 |
| ITF - M25 Aldershot | 2023/08/15 10:25 | Oscar Weightman v Matthew Dellavedova | 3-6,6-2,6-2 |
| ITF - M25 Roehampton | 2023/08/11 11:25 | Oscar Weightman v Paul Jubb | 2-6,6-7 |
| ITF - M25 Roehampton | 2023/08/08 15:05 | Daniel Little v Oscar Weightman | 3-6,6-7 |
| ITF - M15 Monastir | 2023/09/14 08:30 | Demetris Azoides v Luca Wiedenmann | 6-3,3-6,0-6 |
| ITF - M15 Monastir | 2023/09/13 11:35 | Alejandro Bancalari v Luca Wiedenmann | 6-7,1-6 |
| ITF - M15 Allershausen | 2023/08/30 10:00 | Luca Wiedenmann v Kai Lemstra | 3-6,1-6 |
| Challenger - Augsburg | 2023/08/20 11:30 | Hady Habib v Luca Wiedenmann | 6-3,6-7,6-2 |
| ITF - M15 Ueberlingen | 2023/08/17 13:40 | Adrian Oetzbach v Luca Wiedenmann | 6-2,7-5 |
| ITF - M15 Ueberlingen | 2023/08/16 13:50 | Milan Welte v Luca Wiedenmann | 7-5,3-6,4-6 |
| ITF - M15 Eupen | 2023/08/11 16:30 | Luca Wiedenmann v Marc Majdandzic | 4-6,7-5,3-6 |
| ITF - M15 Eupen | 2023/08/10 09:00 | Luca Wiedenmann v Maik Steiner | 3-6,6-3,6-1 |