| Sat15 May2021 |
|  | 11:00 | Cricket 1st XI | v Merchant Taylors' School, Northwood | A |
| | 14:00 | Cricket 4th XI, U14A, U14B, U14C | v Merchant Taylors' School, Northwood | A |
| | 14:00 | Cricket 2nd XI, 3rd XI, U15A, U15B, U15C | v Merchant Taylors' School, Northwood | H |
| | 14:00 | Cricket 2nd XI, 3rd XI, U15A, U15B, U15C | v Merchant Taylors' School, Northwood | H |
|  | 14:15 | Tennis U15B, U14B | v Tonbridge School | H |
| |
| Wed19 May2021 |
| | 14:00 | Cricket U13B, U12B | v Wetherby Preparatory School | H |
| | 14:15 | Cricket U13C, U12D | v Wetherby Preparatory School | H |
| | 14:30 | Tennis U13A, U13B, U12A, U12B | v Epsom College | A |
| |
| Thu20 May2021 |
| | 14:30 | Cricket U15A | v Harrow School | A |
| |
| Fri21 May2021 |
| | 14:00 | Cricket U11A, U11B, U11C, U11D, U10A, U10E | v St Benedict's School | H |
| | 16:15 | Tennis U13A, U12A | v Dulwich College | H |
| |
| Sat22 May2021 |
| | 11:30 | Cricket 1st XI | v Epsom College | A |
| | 14:00 | Cricket 3rd XI, U15A, U15B, U15C | v Epsom College | A |
| | 14:00 | Cricket 2nd XI, U14A, U14B, U14C | v Epsom College | H |
| |
| Thu27 May2021 |
| | 14:30 | Cricket U9A, U9B, U9C, U9D, U9E, U9F | v Dulwich College | H |
| |
| Mon7 Jun2021 |
| | 09:30 | Cricket U12A | v Westminster Under School | H |
| | 14:30 | Cricket U13A, U13B | v Westminster Under School | H |
| | 14:30 | Tennis U13A, U12A | v Westminster Under School | H |
| |
| Tue8 Jun2021 |
| | 14:30 | Cricket U10A, U10B, U10D, U10F | v Donhead, Wimbledon College Preparatory | H |
| | 16:15 | Tennis U10A | v The Harrodian School | H |
| |
| Thu10 Jun2021 |
| | 16:30 | Tennis U13A, U12A | v King's College School (KCS), Wimbledon | A |
| |
| Fri11 Jun2021 |
| | 14:30 | Cricket U11A, U11B, U11C, U11D | v Donhead, Wimbledon College Preparatory | H |
| |
| Sat12 Jun2021 |
| | 09:30 | Cricket 3rd XI, U13A | v Hampton School | A |
| | 11:00 | Cricket 1st XI | v Hampton School | H |
| | 14:00 | Cricket 2nd XI, U15A, U15B, U15C, U13B, U13C | v Hampton School | A |
| | 14:00 | Cricket U14A, U14B, U14C, U12A, U12B, U12C | v Hampton School | H |
| |
| Mon14 Jun2021 |
| | 14:15 | Cricket U13A, U13B, U13C | v King's House School | A |
| | 14:15 | Cricket U12A, U12B | v King's House School | H |
