| Wed23 Sep2020 |
|  | 14:45 | Football 1st XI, 3rd XI | v Gordon's School | A |
| |
| Sat26 Sep2020 |
|  | 10:00 | Rugby Union U12A, U12B, U12C | v RGS, High Wycombe | A |
| | 10:00 | Rugby Union U13A, U13B, U13C | v RGS, High Wycombe | H |
| | 11:15 | Football U17A, U17B | v Whitgift School | A |
| | 11:15 | Football 1st XI, U16A, U16B, U16C | v Whitgift School | H |
| | 11:30 | Rugby Union U16A, U16B, U14A, U14B | v RGS, High Wycombe | H |
| | 12:00 | Rugby Union 1st XV, U15A, U15B | v RGS, High Wycombe | A |
|  | 13:00 | Cricket 1st XI, U16A, U15A | v St George's College, Weybridge | H |
| | 13:30 | Rugby Union 2nd XV | v RGS, High Wycombe | H |
| | 14:15 | Football U18I, U18J, U17A, U17B | v Harrow School | A |
|  | 14:30 | Athletics | Charterhouse Cup | Charterhouse School |
| |
| Mon28 Sep2020 |
| | 14:50 | Football U13A | v Winston Churchill School | H |
| |
| Wed30 Sep2020 |
| | 14:30 | Football 1st XI | v Wilson's School | tbc |
| | 14:45 | Rugby Union 3rd XV | v RGS, High Wycombe | A |
| |
| Sat3 Oct2020 |
| | 09:30 | Rugby Union U12A, U12B, U12C | v St George's College, Weybridge | A |
| | 09:30 | Rugby Union U13A, U13B, U13C | v St George's College, Weybridge | H |
| | 10:00 | Cricket 1st XI, U16A, U15A, U14A | v Tiffin School | H |
| | 10:00 | Football 1st XI, 2nd XI, U15A, U15B, U15C, U13A, U13B, U12A, U12B, U12C, U12D | v Alleyn's School | A |
| | 10:00 | Football 3rd XI, 4th XI, 5th XI, U14A, U14B, U14C | v Alleyn's School | H |
| | 10:30 | Football U15A | v Bede's School | H |
| |
| Wed7 Oct2020 |
| | | Athletics | King's Trophy | Wimbledon Common |
| | 14:30 | Football 3rd XI, U16B | v Salesian College | A |
| |
| Fri9 Oct2020 |
| | 14:50 | Football U12A, U12B, U12C, U12D, U12E, U12F | v Sutton Grammar School for Boys | A |
| |
| Sat10 Oct2020 |
| | 10:00 | Rugby Union U12A, U12B, U12C | v Epsom College | A |
| | 10:00 | Rugby Union U13A, U13B, U13C | v Epsom College | H |
| | 11:00 | Cricket 1st XI | v Eton College | A |
| | 14:00 | Cricket U15A, U14A | v Eton College | A |
| | 14:30 | Football 1st XI, 2nd XI, 3rd XI, 4th XI, U16A, U16B, U15B, U15C, U15D, U14C | v Bradfield College | A |
| | 14:30 | Football U15A, U14A, U14B, U14D | v Bradfield College | H |
| | 14:30 | Rugby Union U16A, U16B, U14A, U14B, U14C | v Epsom College | A |
| | 14:30 | Rugby Union 2nd XV, 3rd XV, U15A, U15B | v Epsom College | H |
| | 14:45 | Rugby Union 1st XV | v Epsom College | H |
| |
| Mon12 Oct2020 |
| | 14:50 | Football U13A | v Radnor House Twickenham | H |
| |
| Tue13 Oct2020 |
| | 14:30 | Football U15B, U15C, U15D, U15E | v Eton College | H |
| |
| Wed14 Oct2020 |
| | 14:30 | Football 3rd XI | v Radnor House Twickenham | A |
| | 14:30 | Football 4th XI | v Radnor House Twickenham | H |
| | 14:30 | Rugby Union 3rd XV | v St Benedict's School | H |
| |
| Thu15 Oct2020 |
| | 14:50 | Football U14A, U14B, U14C, U14D, U14E | v Eton College | H |
| |
| Fri16 Oct2020 |
| | 14:50 | Football U12C | v Radnor House Twickenham | H |
