Stadium: Indoor 1 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 Nottingham | 2023/04/18 09:00 | Daniel Little v Oscar Weightman | 6-4,6-1 |
| UK Pro League | 2022/02/21 14:00 | Daniel Little v Oscar Weightman | 6-7,6-7 |
| ITF M25 Roehampton | 2023/08/02 12:45 | Daniel Little v Luc Koenig | 6-4,5-7,6-7 |
| 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 | Daniel Little v Mark Whitehouse | 3-6,6-7 |
| ITF M25 Nottingham | 2023/07/12 09:45 | Yannik Steinegger v Daniel Little | 6-4,6-4 |
| ATP Eastbourne | 2023/06/24 15:55 | Daniel Little v Beibit Zhukayev | 4-6,4-6 |
| ITF M25 Wichita | 2023/06/14 16:55 | Daniel Little v Aidan Kim | 4-6,1-6 |
| ITF M15 San Diego | 2023/06/08 17:00 | Daniel Little v Trevor Svajda | 4-6,3-6 |
| ITF M15 San Diego | 2023/06/07 16:00 | Daniel Little v Blake Kasday | 6-0,6-3 |
| 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 Londýn | 2023/05/21 10:00 | Oscar Weightman v Luka Petrovic | 7-6,6-2 |
| UTR Pro Londýn | 2023/05/20 08:30 | Oscar Weightman v Luke Simkiss | 6-3,6-0 |
| UTR Pro Londýn | 2023/05/19 07:00 | Oscar Weightman v Jeremy Gschwendtner | 6-2,5-4 |