| Tue11 May2021 |
|  | 14:00 | Cricket 1st XI, 2nd XI, 3rd XI | v Eton College | A |
| | 14:30 | Cricket 4th XI | v Eton College | A |
|  | 15:00 | Tennis U15A, U15B, U15C | v The King's High School for Girls | A |
| | 16:00 | Tennis U14A, U14B, U14C | v The King's High School for Girls | A |
| |
| Wed12 May2021 |
| | 14:30 | Cricket 1st XI | v Magdalen College School | A |
| | 15:45 | Cricket Yearlings A, Yearlings B | v Stowe School | A |
| | 16:00 | Cricket Junior Colts B XI | v Stowe School | H |
| | 16:00 | Tennis U15A | v Magdalen College School | A |
| | 16:15 | Cricket Junior Colts A XI | v Stowe School | H |
| | 16:15 | Tennis U18A, U18B | v The King's High School for Girls | A |
| |
| Thu13 May2021 |
| | 14:00 | Cricket U13B | v Ashfold School | A |
| | 14:00 | Cricket U13A | v Ashfold School | H |
| | 18:15 | Cricket Gentlemen's XI | v Bloxham Common Room XI | H |
| |
| Sat15 May2021 |
| | 10:00 | Cricket U13A, U13B | v Warwick School | H |
|  | 12:30 | Athletics | Rugby School (Mixed) | The Pingles Stadium, Nuneaton |
| | 13:30 | Tennis U18A, U18B | v St Edward's School, Oxford | H |
| | 14:00 | Cricket 1st XI, 3rd XI, Yearlings A, Yearlings B | v Warwick School | A |
| | 14:00 | Cricket 1st XI, 3rd XI, Yearlings A, Yearlings B | v Warwick School | A |
| | 14:00 | Cricket 2nd XI, 2nd XI, Junior Colts A XI, Junior Colts B XI | v Warwick School | H |
| | 14:30 | Tennis U18B, U18C | v Bradfield College | A |
| | 14:30 | Tennis U16A, U16B | v Bradfield College | H |
| |
| Wed19 May2021 |
| | 13:00 | Athletics | Stowe School (Senior) | Stowe School, Buckinghamshire, MK18 5EH |
| | 14:00 | Cricket 3rd XI | v Kingham Hill School | H |
|  | 14:30 | Golf Mixed U18A | v Magdalen College School | H |
| | 14:30 | Tennis U18A, U18B | v Pangbourne College | A |
| | 14:30 | Tennis U18A, U18B | v Pangbourne College | H |
| | 15:45 | Cricket Junior Colts A XI | v Burford School | A |
| |
| Sat22 May2021 |
| | 10:00 | Cricket U13A, U13B | v Magdalen College School | H |
| | 11:30 | Cricket 1st XI | v Magdalen College School | H |
| | 12:30 | Athletics | Bromsgrove School (Mixed) | Bromsgrove School, Worcestershire, B61 7DU |
| | 13:30 | Tennis U13A, U13B | v Tudor Hall School | A |
| | 14:00 | Cricket 2nd XI, 3rd XI, Junior Colts A XI, Junior Colts B XI | v Magdalen College School | A |
| | 14:00 | Cricket Yearlings A, Yearlings B | v Magdalen College School | H |
| | 14:00 | Tennis U15A, U15A, U15B | v Bromsgrove School | A |
| | 14:00 | Tennis U18A, U18A, U18B, U18B, U14A, U14A, U14B | v Bromsgrove School | H |
| | 14:30 | Cricket 4th XI | v Magdalen College School | A |
| | 14:30 | Tennis U18C | v Bromsgrove School | H |
| |
| Tue25 May2021 |
| | 14:00 | Golf Mixed U18A | v St Edward's School, Oxford | H |
| |
| Wed26 May2021 |
| | 14:45 | Cricket Yearlings A, Yearlings B | v Abingdon School | A |
| | 14:45 | Cricket Junior Colts A XI, Junior Colts B XI, Junior Colts C XI | v Abingdon School | H |
| |
| Tue8 Jun2021 |
| | 14:30 | Cricket Yearlings A, Yearlings B | v Warwick School | A |
| |
| Wed9 Jun2021 |
| | 14:30 | Cricket 2nd XI | v Warwick School | A |
| | 14:30 | Cricket 1st XI, 3rd XI | v Warwick School | H |
| | 14:30 | Tennis U18A | v Princethorpe College | H |
| | 15:45 | Cricket Yearlings A | v Burford School | H |
| |
| Thu10 Jun2021 |
| | 14:30 | Cricket U13A, U13B | v Warwick School | A |
| | 14:30 | Tennis U13A, U13B | v Princethorpe College | A |
