| 10 Jun 2001 | First Round | Old Merchant Taylors v Marlborough Blues | Durrants Sports Ground, Croxley Green | Results |
| 10 Jun 2001 | First Round | Sherborne Pilgrims v Bradfield Waifs | Sherborne School, Sherborne | Results |
| 24 Jun 2001 | Second Round | Old Alleynians v Old Merchant Taylors | Dulwich College Ground, Dulwich | Results |
| 24 Jun 2001 | Second Round | Old Tonbridgians v Sherborne Pilgrims | Tonbridge School Ground, Tonbridge | Results |
| 08 Jul 2001 | Quarter-Final | Sherborne Pilgrims v Old Merchant Taylors | Sherborne School, Sherborne | Results |
| 22 Jul 2001 | Semi-Final | Oundle Rovers v Sherborne Pilgrims | Oundle School Ground, Oundle | Results |
| 10 Jun 2001 | First Round | Charterhouse Friars v Old Malvernians | Charterhouse School, Godalming | Results |
| 10 Jun 2001 | First Round | Old Alleynians v Rugby Meteors | Dulwich College Ground, Dulwich | Results |
| 10 Jun 2001 | First Round | Old Blundellians v Old Cliftonians | Blundell's School, Tiverton | Results |
| 10 Jun 2001 | First Round | Old Brightonians v Haileybury Hermits | Brighton College Ground, Brighton | Results |
| 10 Jun 2001 | First Round | Old Cheltonians v Old Amplefordians | College Ground, Cheltenham | Results |
| 10 Jun 2001 | First Round | Old Cholmeleians v Eton Ramblers | Highgate School Ground, Highgate | Results |
| 10 Jun 2001 | First Round | Old Tonbridgians v Felsted Robins | Tonbridge School Ground, Tonbridge | Results |
| 10 Jun 2001 | First Round | Old Wellingtonians v Uppingham Rovers | Wellington College, Crowthorne | Results |
| 10 Jun 2001 | First Round | Old Westminsters v St Edward's Martyrs | Vincent Square, Westminster | Results |
| 10 Jun 2001 | First Round | Old Wykehamists v Downside Wanderers | Ridding Field, Winchester | Results |
| 10 Jun 2001 | First Round | Oundle Rovers v Lancing Rovers | Oundle School Ground, Oundle | Results |
| 10 Jun 2001 | First Round | Repton Pilgrims v Harrow Wanderers | Repton School Ground, Repton | Results |
| 10 Jun 2001 | First Round | Shrewsbury Saracens v Radley Rangers | Shrewsbury School, Shrewsbury | Results |
| 10 Jun 2001 | First Round | Stowe Templars v Old Whitgiftians | Stowe School Ground, Stowe | Results |
| 24 Jun 2001 | Second Round | Harrow Wanderers v Shrewsbury Saracens | Harrow School Cricket Ground, Harrow-on-the-Hill | Results |
| 24 Jun 2001 | Second Round | Old Blundellians v Charterhouse Friars | Blundell's School, Tiverton | Results |
| 24 Jun 2001 | Second Round | Old Brightonians v Old Westminsters | Brighton College Ground, Brighton | Results |
| 24 Jun 2001 | Second Round | Old Wellingtonians v Downside Wanderers | Wellington College, Crowthorne | Results |
| 24 Jun 2001 | Second Round | Oundle Rovers v Old Cheltonians | Oundle School Ground, Oundle | Results |
| 24 Jun 2001 | Second Round | Stowe Templars v Eton Ramblers | Stowe School Ground, Stowe | Results |
| 08 Jul 2001 | Quarter-Final | Harrow Wanderers v Old Wellingtonians | Harrow School Cricket Ground, Harrow-on-the-Hill | Results |
| 08 Jul 2001 | Quarter-Final | Old Brightonians v Eton Ramblers | Brighton College Ground, Brighton | Results |
| 08 Jul 2001 | Quarter-Final | Oundle Rovers v Charterhouse Friars | Oundle School Ground, Oundle | Results |
| 22 Jul 2001 | Semi-Final | Old Wellingtonians v Eton Ramblers | Wellington College, Crowthorne | Results |
| 12 Aug 2001 | Final | Eton Ramblers v Oundle Rovers | Bank of England Ground, Roehampton | Results |
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