| Trinity A | 2 - 4 | Sutton A | Fri 22nd Sep 2023 | 16:30 | Division 1 | Briant Poulter (Surrey Schools) League | OU |
| Trinity B | 6 - 6 | Reigate | Fri 22nd Sep 2023 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
| Dunottar | 7 - 5 | Trinity B | Fri 29th Sep 2023 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
| KCS Wimbledon A | 6 - 0 | Trinity A | Fri 6th Oct 2023 | 16:30 | Division 1 | Briant Poulter (Surrey Schools) League | OU |
| Trinity A | 1 - 5 | Whitgift A | Fri 3rd Nov 2023 | 16:30 | Division 1 | Briant Poulter (Surrey Schools) League | OU |
| Trinity B | 9½ - 2½ | Whitgift B | Fri 3rd Nov 2023 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
| Wilson's D | 10 - 2 | Trinity B | Fri 10th Nov 2023 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
| Trinity A | ½ - 5½ | Wilson's A | Fri 17th Nov 2023 | 16:30 | Division 1 | Briant Poulter (Surrey Schools) League | OU |
| Trinity B | 2½ - 9½ | Wilson's C | Fri 17th Nov 2023 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
| Wilson's C | 4 - 2 | Trinity A | Mon 20th Nov 2023 | 16:00 | Wilsons Qualifier | National Schools | OU |
| Trinity C | 0 - 6 | Tiffin C | Mon 20th Nov 2023 | 16:00 | Wilsons Qualifier | National Schools | OU |
| Cheam | 2 - 4 | Trinity B | Mon 20th Nov 2023 | 16:00 | Wilsons Qualifier | National Schools | OU |
| Trinity A | 5 - 1 | Cheam | Mon 20th Nov 2023 | 17:00 | Wilsons Qualifier | National Schools | OU |
| Trinity B | 2 - 4 | Wilson's C | Mon 20th Nov 2023 | 17:00 | Wilsons Qualifier | National Schools | OU |
| Trinity C | 3 - 3 | Tiffin F | Mon 20th Nov 2023 | 17:00 | Wilsons Qualifier | National Schools | OU |
| Trinity A | 4½ - 1½ | Tiffin C | Mon 20th Nov 2023 | 18:00 | Wilsons Qualifier | National Schools | OU |
| Cheam | 5½ - ½ | Trinity C | Mon 20th Nov 2023 | 18:00 | Wilsons Qualifier | National Schools | OU |
| Tiffin F | 1 - 5 | Trinity B | Mon 20th Nov 2023 | 18:00 | Wilsons Qualifier | National Schools | OU |
| Hampton A | 5½ - ½ | Trinity A | Fri 24th Nov 2023 | 16:30 | Division 1 | Briant Poulter (Surrey Schools) League | OU |
| KCS Under13 | 5½ - ½ | Trinity A | Fri 1st Dec 2023 | 16:30 | Division 1 | Briant Poulter (Surrey Schools) League | OU |
| Emanuel | 11 - 1 | Trinity B | Fri 8th Dec 2023 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
| Reigate | 9 - 3 | Trinity B | Fri 12th Jan 2024 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
| Trinity A | 2 - 4 | KCS Wimbledon B | Fri 19th Jan 2024 | 16:30 | Division 1 | Briant Poulter (Surrey Schools) League | OU |
| Dulwich A | 10 - 2 | Trinity B | Mon 22nd Jan 2024 | 16:30 | Region 20 Rapidplay | National Schools | OU |
| Dulwich A < | 0 - 0 | Trinity B | Mon 22nd Jan 2024 | 16:30 | Region 20 South London | National Schools | OU |
| Trinity A | ½ - 5½ | Wilson's A | Wed 24th Jan 2024 | 16:30 | Region 20 South London | National Schools | OU |
| Trinity B | 3½ - 8½ | Dunottar | Fri 26th Jan 2024 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
| Wilson's B | 6 - 0 | Trinity A | Fri 2nd Feb 2024 | 16:30 | Division 1 | Briant Poulter (Surrey Schools) League | OU |
| Wilson's C | 11½ - ½ | Trinity B | Fri 2nd Feb 2024 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
| Trinity B | 4 - 8 | Emanuel | Fri 23rd Feb 2024 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
| Trinity A | 1½ - 4½ | Hampton B | Fri 1st Mar 2024 | 16:30 | Division 1 | Briant Poulter (Surrey Schools) League | OU |
| Trinity B | 1 - 11 | Wilson's D | Fri 1st Mar 2024 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
| Whitgift B | 6 - 6 | Trinity B | Fri 8th Mar 2024 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
| Guildford A | 5½ - ½ | Trinity A | Fri 15th Mar 2024 | 16:30 | Division 1 | Briant Poulter (Surrey Schools) League | OU |
| Guildford Reserves | ½ - ½ | Trinity Reserves | Fri 15th Mar 2024 | 16:30 | Division 2 Reserves | Briant Poulter (Surrey Schools) League | OU |
