| Wed4 Oct2023 |
|  | 14:15 | Football 7th XI | v Wilson's 2nd XI | H |
| | 14:15 | Football U18B | v Wilson's 7th XI | H |
| | 14:30 | Football U18C | v City of London Freemen's | A |
| | 14:30 | Football U18E | v Freemans | A |
| | 14:30 | Football U18A | v Orleans Park School | A |
|  | 14:30 | Rugby Union 1st XV | v Carshalton Boys Sports College | H |
|  | 14:30 | Table Tennis U16A, U13A | v SGO Competiton | H |
| |
| Thu5 Oct2023 |
| | 14:00 | Football U14A, U14B, U14C | v Carshalton Boys Sports College | H |
|  | 16:15 | Basketball U12A | v Whitgift School | H |
| |
| Fri6 Oct2023 |
| | 14:15 | Football U12A | v Hinchley Wood School | A |
| | 14:30 | Rugby Union U12A | v Carshalton Boys Sports College | A |
|  | 16:30 | Chess D | v Reigate Grammar School | A |
| | 16:30 | Chess A | v Hampton School | H |
| | 17:00 | Chess B | v Hampton School | H |
| |
| Sat7 Oct2023 |
| | 08:00 | FOOTBALL SCHOLARSHIP DAY | |
| |
| Mon9 Oct2023 |
| | 15:00 | Football U14A | v Beacon School | H |
| | 16:00 | Basketball U15A | v John Fisher School | H |
| | 16:00 | Table Tennis U13A | v Whitgift School | A |
| |
| Tue10 Oct2023 |
|  | 14:30 | Badminton U16A | v Epsom College | A |
| | 16:00 | Football U13A, U13B | v ACS International School Cobham | A |
| | 16:15 | Basketball U15A | v Chessington Community College | H |
| |
| Wed11 Oct2023 |
| | 14:00 | Football U18A | v Southborough High School | H |
| | 14:15 | Football U18B, U18D, U18E | v Sutton Grammar School for Boys | A |
| | 14:25 | Rugby Union 1st XV, 1st XV, 1st XV | v Claremont Fan Court School | A |
| | 14:30 | Football U18C | v All Hallows | A |
| | 16:10 | Badminton U16A | v Whitgift School | H |
| |
| Thu12 Oct2023 |
| | 09:15 | 2023 SECONDARY BOROUGH CROSS COUNTRY | |
| | 14:30 | Rugby Union U14A | v Oasis Academy Coulsdon | A |
| | 15:15 | Football U14A | v Christ's School | A |
| | 15:15 | Football U13B | v Southborough High School | A |
| | 16:10 | Basketball U16A | v John Fisher School | A |
| |
| Fri13 Oct2023 |
| | 14:30 | Rugby Union U12A | v King's College School (KCS), Wimbledon | A |
| | 16:30 | Chess D | v Dunottar School | A |
| |
| Sat14 Oct2023 |
| | 09:00 | Football U12A, U12B, U12C, U12D | v Alleyn's School | A |
| | 09:30 | Football U14A, U14B, U14C | v Alleyn's School | A |
| | 09:30 | Football U13A, U13B, U13C | v Alleyn's School | H |
| |
| Mon16 Oct2023 |
| | 15:45 | Rugby Union U15B | v Wallington County Grammar School | H |
| | 16:45 | Basketball U15A | v Alleyn's School | H |
| |
| Tue17 Oct2023 |
| | 14:15 | Rugby Union U13A | v Wallington County Grammar School | A |
| | 16:15 | Football U12A, U12B | v Epsom College | A |
| |
| Wed18 Oct2023 |
| | 14:15 | Rugby Union 2nd XV | v Wallington County Grammar School | H |
| | 14:30 | Football U18B, U18C | v Dulwich College | A |
| | 14:30 | Football 7th XI | v Dulwich | A |
| | 14:30 | Football U18E | v Thomas Vale | H |
| | 15:15 | Football U13B | v Southborough | A |
| |
| Thu19 Oct2023 |
| | 13:30 | Football U12A | v St John's Kent | H |
| | 15:30 | Rugby Union U14A | v Wallington County Grammar School | A |
| | 16:00 | Basketball U13A | v Wimbledon College | H |
| |
| Mon30 Oct2023 |
| | 13:30 | Football U18A | v Coombe Wood | H |
| |
| Wed1 Nov2023 |
| | 14:00 | Football U18A | v Varndean College | A |
