| 02 Jun 1996 | First Round | Bradfield Waifs v Old Cheltonians | Bradfield College, Reading | Results |
| 02 Jun 1996 | First Round | Downside Wanderers v Old Alleynians | Downside School, Stratton-on-the-Fosse | Results |
| 02 Jun 1996 | First Round | Eton Ramblers v Charterhouse Friars | Upper Club, Eton College | Results |
| 02 Jun 1996 | First Round | Haileybury Hermits v Sherborne Pilgrims | Haileybury College Ground, Hertford | Results |
| 02 Jun 1996 | First Round | Harrow Wanderers v Old Malvernians | Harrow School Cricket Ground, Harrow-on-the-Hill | Results |
| 02 Jun 1996 | First Round | Lancing Rovers v Old Amplefordians | Lancing College Ground, Lancing | Results |
| 02 Jun 1996 | First Round | Old Cholmeleians v Rugby Meteors | Highgate School Ground, Highgate | Results |
| 02 Jun 1996 | First Round | Old Cliftonians v Old Brightonians | Clifton College Close Ground, Clifton | Results |
| 02 Jun 1996 | First Round | Old Tonbridgians v Old Merchant Taylors | Tonbridge School Ground, Tonbridge | Results |
| 02 Jun 1996 | First Round | Old Wellingtonians v Uppingham Rovers | Wellington College, Crowthorne | Results |
| 02 Jun 1996 | First Round | Old Westminsters v Shrewsbury Saracens | Vincent Square, Westminster | Results |
| 02 Jun 1996 | First Round | Old Whitgiftians v Felsted Robins | Whitgift School, Croydon | Results |
| 02 Jun 1996 | First Round | Old Wykehamists v Stowe Templars | Ridding Field, Winchester | Results |
| 02 Jun 1996 | First Round | Oundle Rovers v Radley Rangers | Oundle School Ground, Oundle | Results |
| 02 Jun 1996 | First Round | Repton Pilgrims v Old Blundellians | Repton School Ground, Repton | Results |
| 02 Jun 1996 | First Round | St Edward's Martyrs v Marlborough Blues | St Edward's School Ground, Oxford | Results |
| 23 Jun 1996 | Second Round | Bradfield Waifs v St Edward's Martyrs | Bradfield College, Reading | Results |
| 23 Jun 1996 | Second Round | Charterhouse Friars v Oundle Rovers | Charterhouse School, Godalming | Results |
| 23 Jun 1996 | Second Round | Haileybury Hermits v Felsted Robins | Haileybury College Ground, Hertford | Results |
| 23 Jun 1996 | Second Round | Lancing Rovers v Old Alleynians | Lancing College Ground, Lancing | Results |
| 23 Jun 1996 | Second Round | Old Brightonians v Repton Pilgrims | Brighton College Ground, Brighton | Results |
| 23 Jun 1996 | Second Round | Old Cholmeleians v Uppingham Rovers | Highgate School Ground, Highgate | Results |
| 23 Jun 1996 | Second Round | Old Wykehamists v Old Merchant Taylors | Ridding Field, Winchester | Results |
| 23 Jun 1996 | Second Round | Shrewsbury Saracens v Harrow Wanderers | Shrewsbury School, Shrewsbury | Results |
| 07 Jul 1996 | Quarter-Final | Bradfield Waifs v Repton Pilgrims | Bradfield College, Reading | Results |
| 07 Jul 1996 | Quarter-Final | Felsted Robins v Uppingham Rovers | Felsted School Ground, Dunmow | Results |
| 07 Jul 1996 | Quarter-Final | Harrow Wanderers v Charterhouse Friars | Harrow School Cricket Ground, Harrow-on-the-Hill | Results |
| 07 Jul 1996 | Quarter-Final | Lancing Rovers v Old Wykehamists | Lancing College Ground, Lancing | Results |
| 21 Jul 1996 | Semi-Final | Bradfield Waifs v Harrow Wanderers | Bradfield College, Reading | Results |
| 21 Jul 1996 | Semi-Final | Lancing Rovers v Uppingham Rovers | Lancing College Ground, Lancing | Results |
| 04 Aug 1996 | Final | Bradfield Waifs v Uppingham Rovers | Bank of England Ground, Roehampton | Results |
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