| Tue17 Sep2019 |
|  | 15:00 | Rugby Union U14A, U14B, U14C, U14D | v Watford Grammar School for Boys | H |
| | 16:00 | Rugby Union U15A, U15B, U15C, U15D | v Watford Grammar School for Boys | H |
| |
| Wed18 Sep2019 |
|  | 14:30 | Football U18A | v The Reach Free School | H |
| | 14:30 | Rugby Union Rugby 1st XV, Rugby 2nd XV, Rugby 3rd XV | v Watford Grammar School for Boys | A |
| | 14:30 | Rugby Union U16A, U16B, U16C | v Watford Grammar School for Boys | H |
| |
| Wed25 Sep2019 |
| | 14:15 | Football U18A | v Latymer Upper School | H |
|  | 15:30 | Hockey Boys U13A, U13B, U12A, U12B | v Merchant Taylors' Prep (formerly Northwood Prep) | H |
| |
| Thu26 Sep2019 |
| | 16:00 | Football U18A, U18B | v Eton College | H |
| |
| Sat28 Sep2019 |
| | 10:30 | Rugby Union Rugby 1st XV | v Magdalen College School | H |
| | 11:00 | Rugby Union U16A, U16B, U16C, U14A, U14B, U14C, U14D | v Magdalen College School | A |
| | 11:00 | Rugby Union Rugby 2nd XV, Rugby 3rd XV, U15A, U15B, U15C | v Magdalen College School | H |
| |
| Wed2 Oct2019 |
|  | 14:00 | Golf 2nd | v Aldenham School | H |
| | 15:30 | Rugby Union U15A | v Rickmansworth School | A |
| |
| Thu3 Oct2019 |
| | 13:30 | Hockey Boys U15A | v Notting Hill and Ealing High School | H |
| |
| Sat5 Oct2019 |
| | 10:00 | Hockey Boys U12A, U12B | v Reed's School | A |
| | 10:00 | Hockey Boys U13A, U13B, U13C, U13D | v Reed's School | H |
| | 10:30 | Rugby Union U14E | v Brentwood School | H |
| | 10:30 | Rugby Union Rugby 3rd XV, U16C, U16C, U15D, U14D | v Shiplake College | H |
| | 10:30 | Rugby Union Rugby 1st XV, Rugby 2nd XV, U15A, U15B | v University College School (UCS) | A |
| | 10:30 | Rugby Union U16A, U16B, U14A, U14B | v University College School (UCS) | H |
| | 11:30 | Hockey Boys U12C, U12D, U12E, U12F | v Reed's School | A |
| | 14:30 | Rugby Union U15C, U15C, U14C, U14D | v Christ's Hospital | H |
| |
| Wed9 Oct2019 |
| | 10:00 | Rugby Union U14A | v St Albans School | H |
| | 14:00 | Golf | v Mill Hill & Belmont Schools | H |
| | 14:15 | Football U18A, U18B | v Bancroft's School | H |
| | 16:00 | Hockey Boys U12B, U12C | v Sir William Borlase's Grammar School | A |
| | 16:00 | Hockey Boys U13A, U13B, U13C, U12A | v Sir William Borlase's Grammar School | H |
| |
| Sat12 Oct2019 |
| | 10:00 | Hockey Boys U13A, U13B | v Caterham School | A |
| | 10:00 | Hockey Boys U12A, U12B, U12C, U12D | v Caterham School | H |
| | 10:30 | Rugby Union U14A, U14B | v Aylesbury Grammar School | A |
| | 10:30 | Rugby Union Rugby 1st XV, Rugby 2nd XV, U16A, U15A, U15B | v Aylesbury Grammar School | H |
| | 10:30 | Rugby Union U14E | v Brentwood School | A |
| | 10:30 | Rugby Union Rugby 3rd XV, U15D, U14D | v Shiplake College | A |
| | 11:00 | Hockey Boys U13C, U13D | v Caterham School | A |
