| Hampton A | 4½ - 1½ | Whitgift A | Fri 22nd Sep 2023 | 16:30 | Division 1 | Briant Poulter (Surrey Schools) League | OU |
| Reigate | 7 - 5 | Whitgift B | Fri 29th Sep 2023 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
| Whitgift A | 3½ - 2½ | KCS Under13 | Fri 6th Oct 2023 | 16:30 | Division 1 | Briant Poulter (Surrey Schools) League | OU |
| Whitgift B | ½ - 11½ | Emanuel | Fri 6th Oct 2023 | 16:30 | Division 2 East | 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 |
| Whitgift B | 4 - 8 | Wilson's C | Fri 10th Nov 2023 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
| Whitgift A | 4 - 2 | KCS Wimbledon B | Fri 17th Nov 2023 | 16:30 | Division 1 | Briant Poulter (Surrey Schools) League | OU |
| Whitgift A | 4 - 2 | Guildford A | Fri 24th Nov 2023 | 16:00 | Division 1 Rapid | Briant Poulter (Surrey Schools) League | OU |
| Whitgift A | 4 - 2 | Guildford A | Fri 24th Nov 2023 | 16:30 | Division 1 | Briant Poulter (Surrey Schools) League | OU |
| Whitgift B | 4½ - 7½ | Dunottar | Fri 1st Dec 2023 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
| Wilson's B | 3 - 3 | Whitgift A | Fri 8th Dec 2023 | 16:30 | Division 1 | Briant Poulter (Surrey Schools) League | OU |
| Wilson's D | 10 - 2 | Whitgift B | Fri 8th Dec 2023 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
| Emanuel | 9½ - 2½ | Whitgift B | Fri 12th Jan 2024 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
| Whitgift A | 4 - 2 | Hampton B | Fri 19th Jan 2024 | 16:30 | Division 1 | Briant Poulter (Surrey Schools) League | OU |
| Whitgift B | 2 - 10 | Reigate | Fri 19th Jan 2024 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
| Wilson's C | 2½ - 3½ | Whitgift | Tue 23rd Jan 2024 | 16:30 | Region 20 South London | National Schools | OU |
| Sutton A | 3½ - 2½ | Whitgift A | Fri 26th Jan 2024 | 16:30 | Division 1 | Briant Poulter (Surrey Schools) League | OU |
| Dunottar | 0 - 0 | Whitgift B | Fri 2nd Feb 2024 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
| Whitgift | 3 - 3 | Eltham < | Wed 21st Feb 2024 | 16:30 | Region 20 South London | National Schools | OU |
| KCS Wimbledon A | 5 - 1 | Whitgift A | Fri 23rd Feb 2024 | 16:30 | Division 1 | Briant Poulter (Surrey Schools) League | OU |
| Wilson's C | 10½ - 1½ | Whitgift B | 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 |
| Whitgift A | 1 - 5 | Wilson's A | Fri 15th Mar 2024 | 16:30 | Division 1 | Briant Poulter (Surrey Schools) League | OU |
| Whitgift B | 2 - 10 | Wilson's D | Fri 15th Mar 2024 | 16:30 | Division 2 East | Briant Poulter (Surrey Schools) League | OU |
