| Thu8 Jun2023 |
|  | 14:30 | Cricket U15A, U15B, U15C | v Eton College | A |
| | 15:00 | Cricket U14B | v Chesham Grammar School | H |
|  | 15:00 | Tennis U13B | v John Colet School | A |
| |
| Mon12 Jun2023 |
| | 12:00 | Cricket U13A | v Whitgift School | H |
| | 14:30 | Cricket U15A, U15B, U15C | v Berkhamsted School | A |
| | 15:30 | Tennis U15B, U14B | v Berkhamsted School | A |
| | 15:45 | Tennis U12A, U12B | v The Beacon School | A |
| | 16:00 | Tennis U15B, U13B, U13B | v Berkhamsted School | A |
| |
| Tue13 Jun2023 |
| | 14:00 | Cricket U15A | v Aylesbury Grammar School | H |
| | 14:30 | Cricket U13B | v Aylesbury Grammar School | A |
| |
| Wed14 Jun2023 |
| | 14:00 | Cricket U13B | v Chesham Grammar School | A |
| | 14:00 | Cricket U13C | v Chesham Grammar School | H |
| |
| Thu15 Jun2023 |
| | 13:30 | Cricket 1st XI, 2nd XI | v Berkhamsted School | A |
| | 13:30 | Cricket 1st XI, 2nd XI | v Berkhamsted School | A |
| | 14:00 | Cricket U14B | v Aylesbury Grammar School | H |
| | 14:30 | Cricket U12B | v Aylesbury Grammar School | A |
| | 15:45 | Tennis U15A, U15B | v Amersham School | H |
| |
| Mon19 Jun2023 |
| | 10:00 | Midlands A Track and Field Cup Final | Tipton Athletics Club |
| | 14:30 | Cricket U13B | v RGS, High Wycombe | A |
| | 14:30 | Cricket U13C | v RGS, High Wycombe | H |
| |
| Tue20 Jun2023 |
| | 14:00 | Cricket U14A | v St Benedict's School | A |
| | 14:00 | Cricket U14B | v St Benedict's School | H |
| |
| Wed21 Jun2023 |
| | 14:30 | Cricket U12A, U12B, U12C, U12D | v Berkhamsted School | A |
| | 15:00 | Tennis U15B, U13A, U13B | v Great Marlow School | A |
| |
| Thu22 Jun2023 |
| | 11:30 | Cricket 1st XI | v Marylebone Cricket Club (MCC) | H |
| | 14:00 | Cricket U13C | v John Hampden Grammar School | A |
| | 14:00 | Tennis U15A, U13B | v Sir Henry Floyd Grammar School | A |
| | 14:30 | Tennis U13A | v Sir Henry Floyd Grammar School | A |
| |
| Fri23 Jun2023 |
| | 14:30 | Cricket U14A, U14B, U14C | v Berkhamsted School | A |
| |
| Sat24 Jun2023 |
| | 10:00 | Cricket U15A, U15B, U13A, U13B, U12A, U12B, U12C | v Reading Blue Coat School | A |
| | 10:00 | Cricket U14A, U14B | v Reading Blue Coat School | H |
| |
| Mon26 Jun2023 |
| | 10:00 | Cricket 1st XI | v Reading Blue Coat School | A |
| | 14:00 | Cricket U12B | v Chesham Grammar School | A |
| | 14:00 | Cricket U12C | v Chesham Grammar School | H |
| |
| Tue27 Jun2023 |
| | 14:00 | Cricket U15C | v Chesham Grammar School | A |
| | 14:00 | Cricket U15B | v Chesham Grammar School | H |
| | 14:30 | Cricket U12B | v John Hampden Grammar School | A |
| | 15:45 | Tennis U14A, U13A, U12A | v Aylesbury Grammar School | H |
| |
| Wed28 Jun2023 |
| | 14:30 | Cricket U13A, U13B, U13C, U13D | v Berkhamsted School | A |
| | 16:00 | Tennis U15A, U13A | v RGS, High Wycombe | H |
| |
| Thu29 Jun2023 |
| | 14:30 | Cricket U12A | v Aylesbury Grammar School | A |
| |
| Fri30 Jun2023 |
| | 14:00 | Cricket 1st XI | v Headmasters XI | H |
| |
| Tue4 Jul2023 |
| | 15:00 | Tennis U15A, U15B, U14A, U14B | v John Hampden Grammar School | H |
| |
| Wed5 Jul2023 |
| | 14:00 | Cricket 1st XI | v Watford Grammar School for Boys | A |
| | 14:00 | Cricket 2nd XI | v Watford Grammar School for Boys | H |
| |
| Thu6 Jul2023 |
| | 15:00 | Tennis U13A, U13B, U12A, U12B | v John Hampden Grammar School | H |
| |
| Fri7 Jul2023 |
| | tbc | Cricket 1st XI | v Bedford Modern School | A |
