Stadium: Central Court Round: 25 Ground: Hardcourt outdoor
| ITF M25 Roehampton | 2023/08/01 11:00 | Daniel Little v Oscar Weightman | 6-2,5-7,7-6 |
| ITF M25 Roehampton | 2023/07/18 10:00 | Billy Harris v Oscar Weightman | 6-3,6-2 |
| ITF M25 Nottingham | 2023/07/11 13:55 | Daniel Cox v Oscar Weightman | 6-1,7-5 |
| ITF M25 Ajaccio | 2023/07/05 11:50 | Patrick Brady v Oscar Weightman | 7-6,3-6,7-6 |
| ITF M25 Bakio | 2023/06/26 13:55 | Oscar Weightman v Alex Martinez | 6-7,3-6 |
| UTR Pro London | 2023/05/21 10:00 | Oscar Weightman v Luka Petrovic | 7-6,6-2 |
| UTR Pro London | 2023/05/20 08:30 | Oscar Weightman v Luke Simkiss | 6-3,6-0 |
| UTR Pro London | 2023/05/19 07:00 | Oscar Weightman v Jeremy Gschwendtner | 6-2,5-4 |
| ITF M25 Porto | 2023/07/23 09:00 | Tiago Boschmans v Matteo Covato | 6-2,7-5 |