| 15 Jun 2008 | First Round | Charterhouse Friars v Felsted Robins | Charterhouse School, Godalming | Results |
| 15 Jun 2008 | First Round | Downside Wanderers v Shrewsbury Saracens | Downside School, Stratton-on-the-Fosse | Results |
| 15 Jun 2008 | First Round | Haileybury Hermits v Old Merchant Taylors | Haileybury College Ground, Hertford | Results |
| 15 Jun 2008 | First Round | Old Alleynians v Marlborough Blues | Dulwich College Trevor Bailey Sports Ground, Dulwich Common | Results |
| 15 Jun 2008 | First Round | Old Amplefordians v Radley Rangers | Ampleforth College, Ampleforth | Results |
| 15 Jun 2008 | First Round | Old Brightonians v Rugby Meteors | Brighton College Ground, Brighton | Results |
| 15 Jun 2008 | First Round | Old Cranleighans v Lancing Rovers | Jubilee, Cranleigh School | Results |
| 15 Jun 2008 | First Round | Old Malvernians v Eton Ramblers | Malvern College Ground, Malvern | Results |
| 15 Jun 2008 | First Round | Old Wellingtonians v Old Cheltonians | Wellington College, Crowthorne | Results |
| 15 Jun 2008 | First Round | Old Westminsters v Harrow Wanderers | Vincent Square, Westminster | Results |
| 15 Jun 2008 | First Round | Old Whitgiftians v Old Cholmeleians | Whitgift School, Croydon | Results |
| 15 Jun 2008 | First Round | Old Wykehamists v Old Cliftonians | Ridding Field, Winchester | Results |
| 15 Jun 2008 | First Round | Repton Pilgrims v Old Tonbridgians | Repton School Ground, Repton | Results |
| 15 Jun 2008 | First Round | Sherborne Pilgrims v Bradfield Waifs | Sherborne School, Sherborne | Results |
| 15 Jun 2008 | First Round | St Edward's Martyrs v Stowe Templars | St Edward's School Ground, Oxford | Results |
| 15 Jun 2008 | First Round | Uppingham Rovers v Oundle Rovers | Middle Field Pitch 1, Uppingham School | Results |
| 29 Jun 2008 | Second Round | Haileybury Hermits v Downside Wanderers | Haileybury College Ground, Hertford | Results |
| 29 Jun 2008 | Second Round | Old Alleynians v Old Brightonians | Dulwich College Ground, Dulwich | Results |
| 29 Jun 2008 | Second Round | Old Amplefordians v Old Malvernians | Ampleforth College, Ampleforth | Results |
| 29 Jun 2008 | Second Round | Old Cheltonians v Harrow Wanderers | College Ground, Cheltenham | Results |
| 29 Jun 2008 | Second Round | Old Cranleighans v Old Cliftonians | The Lowers, Cranleigh School | Results |
| 29 Jun 2008 | Second Round | Old Tonbridgians v St Edward's Martyrs | Tonbridge School Ground, Tonbridge | Results |
| 29 Jun 2008 | Second Round | Old Whitgiftians v Sherborne Pilgrims | Whitgift School, Croydon | Results |
| 29 Jun 2008 | Second Round | Uppingham Rovers v Felsted Robins | Middle Field Pitch 1, Uppingham School | Results |
| 13 Jul 2008 | Quarter-Final | Old Alleynians v Felsted Robins | Old Alleynians Ground, Dulwich Common | Results |
| 13 Jul 2008 | Quarter-Final | Old Cheltonians v Old Cranleighans | College Ground, Cheltenham | Results |
| 13 Jul 2008 | Quarter-Final | Old Malvernians v Old Tonbridgians | Malvern College Ground, Malvern | Results |
| 13 Jul 2008 | Quarter-Final | Sherborne Pilgrims v Haileybury Hermits | Sherborne School, Sherborne | Results |
| 27 Jul 2008 | Semi-Final | Old Cranleighans v Old Alleynians | Jubilee, Cranleigh School | Results |
| 27 Jul 2008 | Semi-Final | Old Malvernians v Sherborne Pilgrims | Malvern College Ground, Malvern | Results |
| 17 Aug 2008 | Final | Old Cranleighans v Old Malvernians | Old Deer Park, Richmond | Results |
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