Stadium: Campo 2 Round: 14 Ground: Hardcourt outdoor
| 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 - M15 Monastir | 2023/09/13 08:30 | Weightman, Oscar v Matteo Covato | 6-3,6-2 |
| ITF M25 Zaragoza | 2023/10/06 13:10 | Ryan Nijboer v Mathys Erhard | 6-0,4-6,4-6 |
| ITF M25 Zaragoza | 2023/10/05 10:50 | Ryan Nijboer v Minin, Matvey | 6-3,6-2 |
| ITF M25 Zaragoza | 2023/10/04 12:30 | Ryan Nijboer v Mora, Maxime | 6-3,6-3 |
| ITF M25 Sabadell | 2023/09/29 09:30 | Ryan Nijboer v Lopez San Martin, Alvaro | 4-6,4-6 |
| ITF M25 Sabadell | 2023/09/28 08:55 | Ryan Nijboer v John Sperle | 6-3,6-1 |
| ITF M25 Sabadell | 2023/09/27 08:25 | Ryan Nijboer v Benjamin Winter Lopez | 7-6,6-1 |
| ITF M15 Madrid | 2023/09/10 09:00 | Ryan Nijboer v Pablo Masjuan Ginel | 6-4,6-3 |
| ITF M15 Madrid | 2023/09/08 09:25 | Mohamed Safwat v Ryan Nijboer | 5-7,3-6 |