| 13 Jun 2021 | First Round | Old Malvernians v Old Bedfordians | North End Lane, Malvern | Results |
| 13 Jun 2021 | First Round | Harrow Wanderers v Old Cholmeleians | Harrow School Cricket Ground, Harrow-on-the-Hill | Results |
| 13 Jun 2021 | First Round | Haileybury Hermits v Uppingham Rovers | Haileybury College Ground, Hertford | Results |
| 13 Jun 2021 | First Round | Downside Wanderers v Old Cheltonians | Downside School, Stratton-on-the-Fosse | Results |
| 13 Jun 2021 | First Round | Marlborough Blues v Repton Pilgrims | Marlborough College Ground, Marlborough | Results |
| 13 Jun 2021 | First Round | Lancing Rovers v Old Millfieldians | Lancing College Ground, Lancing | Results |
| 13 Jun 2021 | First Round | Old Eastbournians v Bradfield Waifs | Eastbourne College Ground, Eastbourne | Results |
| 13 Jun 2021 | First Round | Sherborne Pilgrims v Old Merchant Taylors | Sherborne School, Sherborne | Results |
| 13 Jun 2021 | First Round | Old Cranleighans v Felsted Robins | Jubilee, Cranleigh School | Results |
| 13 Jun 2021 | First Round | Old Wykehamists v Stowe Templars | Ridding Field, Winchester | Results |
| 13 Jun 2021 | First Round | Oundle Rovers v Charterhouse Friars | Oundle School Ground, Oundle | Results |
| 13 Jun 2021 | First Round | St Edward's Martyrs v Old Wellingtonians | St Edward's School Ground, Oxford | Results |
| 13 Jun 2021 | First Round | Rugby Meteors v Radley Rangers | Rugby School Ground, Rugby | Results |
| 13 Jun 2021 | First Round | Old Hurst Johnians v Old Tonbridgians | Hurstpierpoint College Ground, Hurstpierpoint | Results |
| 13 Jun 2021 | First Round | Old Amplefordians v Eton Ramblers | Ampleforth College, Ampleforth | Results |
| 13 Jun 2021 | First Round | Old Brightonians v Old Alleynians | Spen Cama Memorial Ground, Fulking | Results |
| 27 Jun 2021 | Second Round | Oundle Rovers v St Edward's Martyrs | Oundle School Ground, Oundle | Results |
| 27 Jun 2021 | Second Round | Eton Ramblers v Old Brightonians | Upper Club, Eton College | Results |
| 27 Jun 2021 | Second Round | Old Malvernians v Harrow Wanderers | North End Lane, Malvern | Results |
| 27 Jun 2021 | Second Round | Haileybury Hermits v Old Cheltonians | Haileybury College Ground, Hertford | Results |
| 27 Jun 2021 | Second Round | Marlborough Blues v Old Millfieldians | Marlborough College Ground, Marlborough | Results |
| 27 Jun 2021 | Second Round | Bradfield Waifs v Old Merchant Taylors | Bradfield College, Reading | Results |
| 27 Jun 2021 | Second Round | Old Cranleighans v Stowe Templars | Jubilee, Cranleigh School | Results |
| 27 Jun 2021 | Second Round | Radley Rangers v Old Tonbridgians | Radley College Bigside Ground, Abingdon | Results |
| 11 Jul 2021 | Quarter-Final | Old Cranleighans v Oundle Rovers | Jubilee, Cranleigh School | Results |
| 11 Jul 2021 | Quarter-Final | Old Tonbridgians v Eton Ramblers | Tonbridge School Ground, Tonbridge | Results |
| 11 Jul 2021 | Quarter-Final | Old Malvernians v Old Cheltonians | Malvern College Ground, Malvern | Results |
| 18 Jul 2021 | Quarter-Final (Replay) | Old Merchant Taylors v Old Millfieldians | Merchant Taylors' School Ground, Northwood | Results |
| 25 Jul 2021 | Semi-Final | Old Malvernians v Old Millfieldians | Malvern College Ground, Malvern | Results |
| 25 Jul 2021 | Semi-Final | Oundle Rovers v Eton Ramblers | Oundle School Ground, Oundle | Results |
| 08 Aug 2021 | Final | Old Millfieldians v Oundle Rovers | Arundel Castle Cricket Club Ground, Arundel | Results |
| 06 Jun 2021 | Preliminary Round | Lancing Rovers v Old Cliftonians | Lancing College Ground, Lancing | Results |
| 06 Jun 2021 | Preliminary Round | Bradfield Waifs v Shrewsbury Saracens | Bradfield College, Reading | Results |
| 04 Jul 2021 | Second Round (replay) | Old Merchant Taylors v Bradfield Waifs | Durrants Sports Ground, Croxley Green | Results |
| 11 Jul 2021 | Quarter-Final | Old Millfieldians v Old Merchant Taylors | Millfield School, Street | Results |
| 04 Jul 2021 | Second Round (second replay) | Old Merchant Taylors v Bradfield Waifs | Durrants Sports Ground, Croxley Green | Results |
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