Stadium: Court 6 Round: 25 Ground: Hardcourt outdoor
| 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 | Damian Rodriguez v Henry Searle | 5-7,1-6 |
| UK Pro League | 2023/01/07 13:00 | Ben Jones v Henry Searle | 6-7,4-6 |
| UK Pro League | 2023/01/06 11:00 | Anton Matusevich v Henry Searle | 6-1,6-3 |
| ITF M25 Roehampton | 2023/07/21 09:55 | Johannus Monday v Luke Saville | 6-7,6-7 |
| ITF M25 Roehampton | 2023/07/20 10:00 | Johannus Monday v Ryan James Storrie | 6-3,4-6,6-1 |
| ITF M25 Roehampton | 2023/07/19 10:55 | Johannus Monday v Devin Badenhorst | 7-6,6-4 |
| ITF M25 Roehampton | 2023/07/18 14:20 | Johannus Monday v Finn Murgett | 6-2,6-3 |
| Wimbledon | 2023/06/28 10:00 | Radu Albot v Johannus Monday | 3-6,7-6,6-2 |
| Wimbledon | 2023/06/26 10:00 | Mili Poljicak v Johannus Monday | 6-3,6-7,3-6 |
| Challenger Ilkley | 2023/06/19 17:10 | Raul Brancaccio v Johannus Monday | 6-3,6-3 |
| Challenger Nottingham | 2023/06/11 12:45 | Johannus Monday v Zachary Svajda | 2-6,2-6 |