Stadium: Court 8 Round: 25 Ground: Hardcourt indoor
| Challenger Olbia | 2023/10/15 12:30 | Weightman, Oscar v Ryan Nijboer | 6-2,6-7,4-6 |
| UK Pro League | 2023/10/07 11:30 | Harry Wendelken v Weightman, Oscar | 6-0,0-6,10-5 |
| UK Pro League | 2023/10/06 13:00 | Weightman, Oscar v Patrick Brady | 6-7,3-6 |
| UK Pro League | 2023/10/05 10:00 | Weightman, Oscar v Joshua Goodger | 5-7,6-4,10-7 |
| UK Pro League | 2023/10/03 10:00 | Giles Hussey v Weightman, Oscar | 6-2,6-2 |
| UK Pro League | 2023/10/02 10:00 | Murphy, Brandon v Weightman, Oscar | 3-6,1-6 |
| ITF - M15 Monastir | 2023/09/15 08:30 | Weightman, Oscar v Luca Wiedenmann | 3-6,5-7 |
| ITF - M15 Monastir | 2023/09/14 08:30 | Samir Hamza Reguig v Weightman, Oscar | 1-6,4-6 |
| ITF M25 Edgbaston | 2023/10/20 10:30 | Kyle Edmund v Samuel, Toby | 6-2,7-5 |
| ITF M25 Edgbaston | 2023/10/19 10:45 | Samuel, Toby v Paul Jubb | 7-5,6-7,6-3 |
| ITF M25 Edgbaston | 2023/10/18 11:00 | Samuel, Toby v Tiran Sanghera | 6-3,6-4 |
| ITF M25 Edgbaston | 2023/10/17 10:30 | Samuel, Toby v Phoenix Weir | 6-1,6-2 |
| Challenger Columbus | 2023/09/18 19:25 | Bernard Tomic v Samuel, Toby | 6-0,6-4 |
| Challenger Columbus | 2023/09/17 21:55 | Bryce Nakashima v Samuel, Toby | 3-6,6-7 |
| Challenger Cary | 2023/09/15 19:00 | Zachary Svajda v Samuel, Toby | 7-5,5-7,6-1 |
| Challenger Cary | 2023/09/13 18:40 | Samuel, Toby v Illya Marchenko | 7-5,6-7,6-1 |