Stadium: Centre Court Round: 26 Ground: Hardcourt outdoor
| ITF M25 Aldershot | 2023/08/16 08:55 | Ben Jones v Henry Searle | 2-6,4-6 |
| ITF M25 Roehampton | 2023/08/01 09:00 | Henry Searle v Monday, Johannus | 6-7,6-3,3-6 |
| ITF - M25 Nottingham | 2023/04/19 12:10 | Patrick Brady v Henry Searle | 6-2,7-5 |
| ITF - M15 Monastir | 2023/03/28 09:55 | Christoph Negritu v Henry Searle | 6-2,6-3 |
| ITF - M15 Monastir | 2023/03/23 08:30 | Henry Searle v Nicolas Tepmahc | 3-6,4-6 |
| ITF - M15 Monastir | 2023/03/21 10:00 | Jasza Szajrych v Henry Searle | 5-7,1-6 |
| ITF - M25 Loughborough | 2023/01/12 10:00 | Henry Searle v Patrick Brady | 0-6,3-6 |
| ITF - M25 Loughborough | 2023/01/10 12:25 | Rodriguez, Damian v Henry Searle | 5-7,1-6 |
| ITF M25 Aldershot | 2023/08/15 10:25 | Weightman, Oscar v Matthew Dellavedova | 3-6,6-2,6-2 |
| ITF M25 Roehampton | 2023/08/11 11:25 | Weightman, Oscar v Paul Jubb | 2-6,6-7 |
| ITF M25 Roehampton | 2023/08/08 15:05 | Daniel Little v Weightman, Oscar | 3-6,6-7 |
| ITF M25 Roehampton | 2023/08/01 11:00 | Daniel Little v Weightman, Oscar | 6-2,5-7,7-6 |
| ITF M25 Roehampton | 2023/07/18 10:00 | Billy Harris v Weightman, Oscar | 6-3,6-2 |
| ITF - M25 Nottingham | 2023/07/11 13:55 | Daniel Cox v Weightman, Oscar | 6-1,7-5 |
| ITF M25 Ajaccio | 2023/07/05 11:50 | Patrick Brady v Weightman, Oscar | 7-6,3-6,7-6 |
| ITF M25 Bakio | 2023/06/26 13:55 | Weightman, Oscar v Martinez, Alex | 6-7,3-6 |