| Sat16 Nov2019 |
|  | 09:30 | Football 1st XI, Sixth Form, U16 (A) | v Merchant Taylors' School, Northwood | A |
| | 09:30 | Football U15A, U14A, U13A, U12A | v Kew House School | H |
| |
| Thu21 Nov2019 |
| | 14:15 | Football U14A | v Alleyn's School | A |
| | 14:45 | Football U14A | v Alleyn's School | H |
| |
| Sat23 Nov2019 |
| | 10:00 | Football 1st XI, Sixth Form, U16 (A) | v Whitgift School | A |
| | 10:00 | Football U16 (B), U15A, U15B, U14A, U14B | v Whitgift School | H |
| | 10:00 | Football U13A, U13B, U12A, U12B, U12C | v Dr Challoner's Grammar School | A |
| |
| Sat30 Nov2019 |
| | 10:00 | Football U15A, U15B, U14A, U14B, U13A, U13B, U12A, U12B | v Kimbolton School | A |
| | 10:00 | Football 1st XI, Sixth Form, U16 (A), U16 (B) | v Kimbolton School | H |
| | 10:00 | Football U15A, U15B, U14A, U14B, U13A, U13B, U12A, U12B | v Kimbolton School | A |
| | 10:00 | Football U15A, U15B, U14A, U14B, U13A, U13B, U12A, U12B | v Highgate School | A |
| | 10:00 | Football 1st XI, Sixth Form, U16 (A), U16 (B) | v Highgate School | H |
| | 10:00 | Football U15A, U15B, U14A, U14B, U13A, U13B, U12A, U12B | v Highgate School | A |
| |
| Tue3 Dec2019 |
| | 14:30 | Football U15A, U14A | v City of London School | H |
| |
| Wed4 Dec2019 |
|  | 14:30 | Hockey 1st XI | v Reading Blue Coat School | H |
| |
| Thu5 Dec2019 |
| | 14:30 | Football U15A, U15B | v Wetherby Senior School | A |
| |
| Sat7 Dec2019 |
| | 09:30 | Football U15A, U15B, U14A, U14B | v Hampton School | A |
| | 09:30 | Football 1st XI, Sixth Form, U16 (A), U13A, U13B, U12A, U12B | v Hampton School | H |
| |
| Mon9 Dec2019 |
| | 14:00 | Football U13B, U12B | v Radnor House Twickenham | A |
| |
| Tue10 Dec2019 |
| | 14:30 | Football U14B | v Radnor House Twickenham | H |
| |
| Wed11 Dec2019 |
| | 14:30 | Football U16 (A), U16 (B) | v Radnor House Twickenham | A |
| |
| Thu12 Dec2019 |
| | 14:30 | Football U15B | v Radnor House Twickenham | H |
