| Mon26 Aug2019 |
|  | 09:00 | Football 1st XI, 1st XI | v Colchester pre-season training Camp | A |
| | 09:00 | Football 1st XI, 1st XI | v Colchester pre-season training Camp | A |
| |
| Tue27 Aug2019 |
| | 16:00 | Football U16A | v Heybridge Town | A |
| | 17:00 | Football 1st XI | v Braintree Town U17 | A |
| | 18:30 | Football 1st XI | v Braintree Town FC U18 | A |
| |
| Wed28 Aug2019 |
| | 17:00 | Football 1st XI | v Cambridge United U17 | A |
| | 18:30 | Football 1st XI | v Cambridge United FC U18 | A |
| | 19:00 | Football U16A | v Heybridge Town EJA | A |
| |
| Sat31 Aug2019 |
|  | 15:30 | Rugby Union 1st XV | v 2019 Leavers XV | H |
| | tbc | Football 1st XI | v Alleyn's School | A |
| |
| Sun1 Sep2019 |
| | tbc | Rugby Union U15A | v South Coast Kings | A |
| |
| Mon2 Sep2019 |
| | 15:30 | Football 1st XI | v Recent leavers Xl | H |
| |
| Wed4 Sep2019 |
| | 17:45 | Football 1st XI | v Corinthian Casuals | H |
| |
| Sat7 Sep2019 |
| | 09:00 | Primary School's 5-a-side Tournament | Hampton School |
| | 09:15 | Football U12A, U12B, U12C | v Rokeby School, Surrey | H |
| | 09:30 | Football U13A, U13B | v Rokeby School, Surrey | A |
| | 10:30 | Rugby Union U16A, U16B, U14A, U14B | v John Fisher School | A |
| | 10:30 | Rugby Union U15A, U15B, U13A, U13B | v John Fisher School | H |
| | 14:00 | Rugby Union 1st XV, 2nd XV, 3rd XV | v John Fisher School | H |
| |
| Sun8 Sep2019 |
|  | 10:00 | Football Sixes U18A | v Bradfield College | A |
| | 10:40 | Football Sixes U18A | v Queen Ethelburga's | A |
| | 11:20 | Football Sixes U18A | v University College School (UCS) | A |
| | 13:20 | Football Sixes U18A | v Westminster School | A |
| | 14:00 | Football Sixes U18A | v Ardingly College | A |
| |
| Mon9 Sep2019 |
|  | 16:15 | Badminton U16A | v King's College School (KCS), Wimbledon | H |
| |
| Wed11 Sep2019 |
|  | 13:30 | Basketball Seniors | v St John the Baptist School | H |
| | 14:30 | Football 1st XI | v Hampton and Richmond FC | H |
| |
| Sat14 Sep2019 |
| | 09:30 | Football U13A, U13B | v Glyn School | A |
| | 09:30 | Football U12A, U12B | v Glyn School | H |
| | 10:00 | Rugby Union U13A, U13B, U13C, U12A, U12B, U12C | v St John's School, Leatherhead | A |
| | 10:30 | Football 1st XI, U15A, U15B, U15C, U14A, U14B, U14C | v Bede's School | A |
| | 10:30 | Football 2nd XI, 3rd XI, 4th XI | v Bede's School | H |
| | 14:00 | Rugby Union 1st XV, 2nd XV, U16A, U16B, U15A, U15B, U14A, U14B | v St John's School, Leatherhead | A |
| | 15:00 | Rugby Union 1st XV | v Tonbridge School | A |
| | 15:00 | Rugby Union 2nd XV, U16A, U16B, U15A, U15B, U14A, U14B | v Tonbridge School | tbc |
| |
| Sun15 Sep2019 |
|  | 16:00 | Chess U18A, U18A | v Eton College | A |
| |
| Wed18 Sep2019 |
| | 14:30 | Badminton 1st | v King's College School (KCS), Wimbledon | A |
| | 14:30 | Rugby Union 3rd XV | v St Benedict's School | H |
| |
| Fri20 Sep2019 |
| | 16:00 | Chess U18A, U18A | v Royal Russell School | A |
| |
| Sat21 Sep2019 |
| | 09:30 | Football U13A, U13B, U13C, U13D, U13E | v Sutton Grammar School for Boys | A |
| | 09:30 | Football U12A, U12B, U12C, U12D, U12E | v Sutton Grammar School for Boys | H |
| | 14:15 | Football 1st XI, 2nd XI, 3rd XI, 4th XI, 5th XI, U15A, U15B, U14A, U14B, U14C, U14D | v Eton College | A |
| | 14:15 | Football U16A, U16B, U15C, U15D | v Eton College | H |
| | 14:30 | Rugby Union 1st XV, 2nd XV, 3rd XV, U15A, U15B | v Cranleigh School | A |
| | 14:30 | Rugby Union U16A, U16B, U14A, U14B | v Cranleigh School | H |
