Stadium: Central Court Round: 25 Ground: Hardcourt outdoor
| 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 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 - M15 Monastir | 2023/08/29 10:35 | Ilia Simakin v Matteo Covato | 6-2,6-3 |
| ITF - M15 Monastir | 2023/08/22 09:50 | Younes Lalami Laaroussi v Matteo Covato | 6-2,6-4 |
| ITF - M15 Monastir | 2023/08/13 12:00 | Matteo Covato v Alvaro Dagoberto Garcia Ramirez | 2-6,6-2,10-2 |
| ITF M25 Porto | 2023/07/23 09:00 | Tiago Boschmans v Matteo Covato | 6-2,7-5 |