| Fri23 Aug2019 |
| | 00:00 | Fencing: Summer Camp | |
| |
| Fri30 Aug2019 |
|  | 14:00 | Rugby Union 1st XV | v Esher Presidents Cup | A |
| |
| Sat31 Aug2019 |
|  | 10:00 | Football 1st XI, 2nd XI | v Kinetic Academy | H |
| | 10:00 | Rugby Union U16A | v Pre Season Tournament | A |
| | 10:00 | Rugby Union U14A | v Pre Season Tournaments | A |
| | 11:00 | Rugby Union U15A | v Pre Season Tournament | A |
| | 11:30 | Rugby Union U16C | v Pre Season Tournaments | A |
| |
| Sun1 Sep2019 |
|  | 13:00 | Cricket U15A | v U15 ESCA t20 Finals Day | A |
| |
| Fri6 Sep2019 |
| | 16:00 | Rugby Union 3rd XV, 4th XV, U16B, U16C | v Training Game | H |
|  | 17:00 | Water Polo U18A | v Dulwich College | H |
| |
| Sat7 Sep2019 |
| | | Fencing: Cadet Sabre BRC, Leon Paul Centre, West Hendon | |
|  | 09:00 | Hockey Boys U15A | v The Portsmouth Grammar School | A |
| | 09:30 | Football U13A | v TWGSB | A |
| | 09:30 | Football U14B, U13B | v Tunbridge Wells Grammar School for Boys | A |
| | 09:30 | Rugby Union U13A, U13B, U13C, U13D, U12A, U12B, U12C, U12D, U12E, U12F | v Training Game | H |
| | 10:00 | Football 2nd XI | v Westminster School | A |
| | 10:00 | Football 1st XI, 3rd XI, U16B | v Westminster School | H |
| | 10:00 | Football U15B, U15C | v Westminster City School | A |
| | 10:00 | Hockey Boys U14A | v The Portsmouth Grammar School | A |
| | 10:30 | Rugby Union U15B, U15C, U14B, U14C, U14D | v Training Games | H |
| | 11:00 | Hockey Boys U16A | v The Portsmouth Grammar School | A |
| | 12:00 | Rugby Union 2nd XV, U15A | v 4 wayer ( Sedbergh/Warwick/Bromsgrove) | A |
| | 13:00 | Rugby Union U14A | v 3 wayer ( Bromsgrove and Warwick) | A |
| | 13:00 | Rugby Union U16A | v 4 wayer ( Sedbergh/Warwick/Bromsgrove) | A |
| |
| Sun8 Sep2019 |
| | 12:00 | Rugby Union 1st XV | v Sedbergh School | A |
| |
| Mon9 Sep2019 |
|  | 16:15 | Hockey Indoor U13A | v Trinity School, Croydon | H |
| |
| Tue10 Sep2019 |
|  | 14:30 | Golf U18A | v Lingfield College | A |
| |
| Wed11 Sep2019 |
| | 14:30 | Golf U18A | v Gordon's School | H |
| | 14:30 | Hockey 1st XI | v Oxford Uni | H |
| | 14:45 | Rugby Union 3rd XV | v Harris City Academy Crystal Palace | H |
|  | 16:45 | Basketball U16B | v Farringtons School | H |
| |
| Thu12 Sep2019 |
| | 14:30 | Football U13A | v Bacon's College | H |
| | 16:00 | Golf U13A | v Reed's School | A |
| |
| Fri13 Sep2019 |
| | 16:45 | Basketball U18B | v Farringtons School | H |
| | 17:00 | Water Polo U18A | v Dulwich College | H |
| | 20:00 | Hockey Boys U14A | v Surbiton HC | A |
| |
| Sat14 Sep2019 |
| | 09:30 | Hockey Boys U13A, U13B | v Caterham School | A |
| | 09:30 | Hockey Boys U14B | v St James Boys Schools | H |
| | 09:30 | Rugby Union U12A, U12B, U12C | v Reigate Grammar School | A |
| | 09:30 | Rugby Union U13A | v Reigate Grammar School | H |
| | 10:00 | Football U16B, U15A, U15B, U14A, U14B, U13A, U13B, U13C | v Forest School | A |
| | 10:00 | Football 1st XI, 2nd XI, 3rd XI | v Forest School | H |
| | 10:30 | Rugby Union U16A | v Gravesend Grammar School for Boys | H |
| | 10:30 | Rugby Union 1st XV, 3rd XV | v Wimbledon College | H |
| | 11:00 | Fencing: Whitgift v Brentwood (A) | Brentwood School |
| | 11:00 | Rugby Union U16B | v Wimbledon College | A |
| | 11:30 | Hockey Boys U16A, U15A | v Squad Matches | H |
| | 14:30 | Rugby Union U16C, U14B, U14C, U14D | v Christ's Hospital | A |
| | 14:30 | Rugby Union 2nd XV, 4th XV, U15B, U15C, U13B, U13C, U13D | v Christ's Hospital | H |
| |
| Mon16 Sep2019 |
| | 14:30 | Rugby Union U14A | v Warden Park | H |
| | 16:15 | Hockey Boys U14A | v Sir William Borlase's Grammar School | A |
| | 16:30 | Football U14B | v Alleyn's School | A |
| | 17:00 | Basketball U18A | v Sevenoaks School | A |
| | 17:00 | Water Polo U15A | v Dulwich College | A |
| |
| Tue17 Sep2019 |
| | 15:00 | Football U15A, U15B | v Alleyn's School | H |
| | 16:45 | Basketball U14A | v Royal Russell School | A |
| |
| Wed18 Sep2019 |
| | 14:30 | Football 1st XI, 2nd XI, 3rd XI | v Wilson's School | A |
| | 14:30 | Golf U18A | v Eltham College | A |
| | 14:30 | Hockey 1st XI | v Nottigham Uni | H |
| | 16:15 | Football U11A, U11B | v Trinity School, Croydon | H |
| | 17:00 | Basketball U15A | v Dulwich College | H |
| |
| Thu19 Sep2019 |
| | 09:30 | Golf U13A | v ISGA Junior Schools Cup | A |
| | 14:30 | Rugby Union U13A, U13B, U13C, U13D | v King's College School (KCS), Wimbledon | H |
|  | 16:00 | Swimming U18A, U16A, U15A, U14A, U13A, U12A, U11A | v Whitgift Cub Championships | H |
| | 16:15 | Golf U15A | v Reed's School | H |
| | 16:45 | Hockey Boys U13A | v Surbiton HC | A |
| |
| Sat21 Sep2019 |
| | | Fencing: Cadet/Junior Nationals, Sports Dock, East London | |
| | 10:30 | Rugby Union U13A, U13B, U12A, U12B | v Training Game | H |
| | 15:00 | Rugby Union 1st XV, 2nd XV, 3rd XV, 4th XV, U15A, U15B, U15C | v Wellington College | A |
| | 15:00 | Rugby Union U16A, U16B, U16C, U14A, U14B, U14C, U14D | v Wellington College | H |
| |
| Sun22 Sep2019 |
| | | Fencing: Cadet/Junior Nationals, Sports Dock, East London | |
