| 02 Jun 1991 | First Round | Old Wellingtonians v Sherborne Pilgrims | Wellington College, Crowthorne | Results |
| 02 Jun 1991 | First Round | St Edward's Martyrs v Uppingham Rovers | St Edward's School Ground, Oxford | Results |
| 02 Jun 1991 | First Round | Old Cheltonians v Old Tonbridgians | College Ground, Cheltenham | Results |
| 02 Jun 1991 | First Round | Old Cliftonians v Old Blundellians | Clifton College Close Ground, Clifton | Results |
| 02 Jun 1991 | First Round | Old Brightonians v Old Malvernians | Brighton College Ground, Brighton | Results |
| 02 Jun 1991 | First Round | Harrow Wanderers v Old Merchant Taylors | Harrow School Cricket Ground, Harrow-on-the-Hill | Results |
| 02 Jun 1991 | First Round | Haileybury Hermits v Downside Wanderers | Haileybury College Ground, Hertford | Results |
| 02 Jun 1991 | First Round | Old Whitgiftians v Charterhouse Friars | Whitgift School, Croydon | Results |
| 02 Jun 1991 | First Round | Old Westminsters v Marlborough Blues | Vincent Square, Westminster | Results |
| 02 Jun 1991 | First Round | Rugby Meteors v Lancing Rovers | Rugby School Ground, Rugby | Results |
| 02 Jun 1991 | First Round | Old Cholmeleians v Repton Pilgrims | Highgate School Ground, Highgate | Results |
| 02 Jun 1991 | First Round | Shrewsbury Saracens v Old Alleynians | Shrewsbury School, Shrewsbury | Results |
| 02 Jun 1991 | First Round | Felsted Robins v Bradfield Waifs | Felsted School Ground, Dunmow | Results |
| 02 Jun 1991 | First Round | Radley Rangers v Old Wykehamists | Radley College Bigside Ground, Abingdon | Results |
| 02 Jun 1991 | First Round | Eton Ramblers v Stowe Templars | Agar's Plough, Eton College | Results |
| 16 Jun 1991 | First Round | Oundle Rovers v Old Amplefordians | Oundle School Ground, Oundle | Results |
| 23 Jun 1991 | Second Round | Uppingham Rovers v Old Tonbridgians | Middle Field Pitch 1, Uppingham School | Results |
| 23 Jun 1991 | Second Round | Shrewsbury Saracens v Bradfield Waifs | Shrewsbury School, Shrewsbury | Results |
| 30 Jun 1991 | Second Round (Replay) | Old Tonbridgians v Uppingham Rovers | Tonbridge School Ground, Tonbridge | Results |
| 30 Jun 1991 | Second Round | Old Brightonians v Old Cliftonians | Brighton College Ground, Brighton | Results |
| 30 Jun 1991 | Second Round | Haileybury Hermits v Harrow Wanderers | Haileybury College Ground, Hertford | Results |
| 30 Jun 1991 | Second Round | Old Wellingtonians v Oundle Rovers | Wellington College, Crowthorne | Results |
| 30 Jun 1991 | Second Round | Old Westminsters v Charterhouse Friars | Vincent Square, Westminster | Results |
| 30 Jun 1991 | Second Round | Repton Pilgrims v Rugby Meteors | Repton School Ground, Repton | Results |
| 30 Jun 1991 | Second Round | Eton Ramblers v Radley Rangers | Upper Club, Eton College | Results |
| 07 Jul 1991 | Quarter-Final | Old Tonbridgians v Old Brightonians | Tonbridge School Ground, Tonbridge | Results |
| 07 Jul 1991 | Quarter-Final | Harrow Wanderers v Oundle Rovers | Harrow School Cricket Ground, Harrow-on-the-Hill | Results |
| 07 Jul 1991 | Quarter-Final | Charterhouse Friars v Repton Pilgrims | Charterhouse School, Godalming | Results |
| 07 Jul 1991 | Quarter-Final | Bradfield Waifs v Eton Ramblers | Bradfield College, Reading | Results |
| 21 Jul 1991 | Semi-Final | Old Tonbridgians v Oundle Rovers | Tonbridge School Ground, Tonbridge | Results |
| 21 Jul 1991 | Semi-Final | Charterhouse Friars v Eton Ramblers | Charterhouse School, Godalming | Results |
| 04 Aug 1991 | Final | Charterhouse Friars v Old Tonbridgians | Vincent Square, Westminster | Results |
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