| 14 Jun 2009 | First Round | Old Cranleighans v Haileybury Hermits | The Lowers, Cranleigh School | Results |
| 14 Jun 2009 | First Round | Harrow Wanderers v Charterhouse Friars | Harrow School Cricket Ground, Harrow-on-the-Hill | Results |
| 14 Jun 2009 | First Round | Lancing Rovers v Stowe Templars | Lancing College Ground, Lancing | Results |
| 14 Jun 2009 | First Round | Old Alleynians v Felsted Robins | Dulwich College Ground, Dulwich | Results |
| 14 Jun 2009 | First Round | Old Amplefordians v Bradfield Waifs | Ampleforth College, Ampleforth | Results |
| 14 Jun 2009 | First Round | Old Brightonians v Uppingham Rovers | Brighton College Ground, Brighton | Results |
| 14 Jun 2009 | First Round | Old Cholmeleians v Old Merchant Taylors | Highgate School Ground, Highgate | Results |
| 14 Jun 2009 | First Round | Old Cliftonians v Old Cheltonians | Clifton College Close Ground, Clifton | Results |
| 14 Jun 2009 | First Round | Old Tonbridgians v Marlborough Blues | Tonbridge School Ground, Tonbridge | Results |
| 14 Jun 2009 | First Round | Old Westminsters v Old Wellingtonians | Vincent Square, Westminster | Results |
| 14 Jun 2009 | First Round | Old Whitgiftians v Eton Ramblers | Whitgift School, Croydon | Results |
| 14 Jun 2009 | First Round | Radley Rangers v Old Wykehamists | Radley College Bigside Ground, Abingdon | Results |
| 14 Jun 2009 | First Round | Repton Pilgrims v Old Malvernians | Repton School Ground, Repton | Results |
| 14 Jun 2009 | First Round | Rugby Meteors v Downside Wanderers | Rugby School Ground, Rugby | Results |
| 14 Jun 2009 | First Round | Sherborne Pilgrims v Oundle Rovers | Sherborne School, Sherborne | Results |
| 14 Jun 2009 | First Round | Shrewsbury Saracens v St Edward's Martyrs | Shrewsbury School, Shrewsbury | Results |
| 28 Jun 2009 | Second Round | Charterhouse Friars v Old Alleynians | Charterhouse School, Godalming | Results |
| 28 Jun 2009 | Second Round | Old Cliftonians v Shrewsbury Saracens | Clifton College Close Ground, Clifton | Results |
| 28 Jun 2009 | Second Round | Old Merchant Taylors v Eton Ramblers | Durrants Sports Ground, Croxley Green | Results |
| 28 Jun 2009 | Second Round | Old Tonbridgians v Old Cranleighans | Tonbridge School Ground, Tonbridge | Results |
| 28 Jun 2009 | Second Round | Old Wellingtonians v Bradfield Waifs | Wellington College, Crowthorne | Results |
| 28 Jun 2009 | Second Round | Oundle Rovers v Radley Rangers | Oundle School Ground, Oundle | Results |
| 28 Jun 2009 | Second Round | Rugby Meteors v Uppingham Rovers | Rugby School Ground, Rugby | Results |
| 28 Jun 2009 | Second Round | Stowe Templars v Repton Pilgrims | Stowe School Ground, Stowe | Results |
| 12 Jul 2009 | Quarter-Final | Charterhouse Friars v Old Tonbridgians | Charterhouse School, Godalming | Results |
| 12 Jul 2009 | Quarter-Final | Eton Ramblers v Old Wellingtonians | Upper Club, Eton College | Results |
| 12 Jul 2009 | Quarter-Final | Old Cliftonians v Oundle Rovers | Clifton College Close Ground, Clifton | Results |
| 12 Jul 2009 | Quarter-Final | Uppingham Rovers v Repton Pilgrims | Middle Field Pitch 1, Uppingham School | Results |
| 26 Jul 2009 | Semi-Final | Oundle Rovers v Old Tonbridgians | Oundle School Ground, Oundle | Results |
| 02 Aug 2009 | Semi-Final (Replay) | Eton Ramblers v Repton Pilgrims | Upper Club, Eton College | Results |
| 16 Aug 2009 | Final | Old Tonbridgians v Repton Pilgrims | Old Deer Park, Richmond | Results |
| 26 Jul 2009 | Semi-Final | Repton Pilgrims v Eton Ramblers | Repton School Ground, Repton | Results |
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