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