| 18 Jun 2000 | First Round | Charterhouse Friars v Old Westminsters | Charterhouse School, Godalming | Results |
| 18 Jun 2000 | First Round | Haileybury Hermits v Oundle Rovers | Haileybury College Ground, Hertford | Results |
| 18 Jun 2000 | First Round | Lancing Rovers v Old Cheltonians | Lancing College Ground, Lancing | Results |
| 18 Jun 2000 | First Round | Old Alleynians v Stowe Templars | Dulwich College Ground, Dulwich | Results |
| 18 Jun 2000 | First Round | Old Amplefordians v Old Tonbridgians | Ampleforth College, Ampleforth | Results |
| 18 Jun 2000 | First Round | Old Blundellians v Bradfield Waifs | Blundell's School, Tiverton | Results |
| 18 Jun 2000 | First Round | Old Cliftonians v Old Whitgiftians | Clifton College Close Ground, Clifton | Results |
| 18 Jun 2000 | First Round | Old Malvernians v Marlborough Blues | Malvern College Ground, Malvern | Results |
| 18 Jun 2000 | First Round | Old Wellingtonians v Old Brightonians | Wellington College, Crowthorne | Results |
| 18 Jun 2000 | First Round | Old Wykehamists v Downside Wanderers | Ridding Field, Winchester | Results |
| 18 Jun 2000 | First Round | Radley Rangers v Harrow Wanderers | Radley College Bigside Ground, Abingdon | Results |
| 18 Jun 2000 | First Round | Repton Pilgrims v Old Merchant Taylors | Repton School Ground, Repton | Results |
| 18 Jun 2000 | First Round | Rugby Meteors v Sherborne Pilgrims | Rugby School Ground, Rugby | Results |
| 18 Jun 2000 | First Round | Shrewsbury Saracens v Felsted Robins | Shrewsbury School, Shrewsbury | Results |
| 18 Jun 2000 | First Round | St Edward's Martyrs v Eton Ramblers | St Edward's School Ground, Oxford | Results |
| 18 Jun 2000 | First Round | Uppingham Rovers v Old Cholmeleians | Middle Field Pitch 1, Uppingham School | Results |
| 02 Jul 2000 | Second Round | Bradfield Waifs v Old Whitgiftians | Bradfield College, Reading | Results |
| 02 Jul 2000 | Second Round | Charterhouse Friars v Sherborne Pilgrims | Charterhouse School, Godalming | Results |
| 02 Jul 2000 | Second Round | Lancing Rovers v Downside Wanderers | Lancing College Ground, Lancing | Results |
| 02 Jul 2000 | Second Round | Old Merchant Taylors v Uppingham Rovers | Durrants Sports Ground, Croxley Green | Results |
| 02 Jul 2000 | Second Round | Old Wellingtonians v Eton Ramblers | Wellington College, Crowthorne | Results |
| 02 Jul 2000 | Second Round | Oundle Rovers v Old Tonbridgians | Oundle School Ground, Oundle | Results |
| 02 Jul 2000 | Second Round | Radley Rangers v Old Malvernians | Radley College Bigside Ground, Abingdon | Results |
| 02 Jul 2000 | Second Round | Stowe Templars v Shrewsbury Saracens | Stowe School Ground, Stowe | Results |
| 16 Jul 2000 | Quarter-Final | Bradfield Waifs v Old Malvernians | Bradfield College, Reading | Results |
| 16 Jul 2000 | Quarter-Final | Charterhouse Friars v Lancing Rovers | Charterhouse School, Godalming | Results |
| 16 Jul 2000 | Quarter-Final | Eton Ramblers v Old Merchant Taylors | Upper Club, Eton College | Results |
| 16 Jul 2000 | Quarter-Final | Shrewsbury Saracens v Old Tonbridgians | Shrewsbury School, Shrewsbury | Results |
| 20 Aug 2000 | Final | Charterhouse Friars v Old Tonbridgians | Bank of England Ground, Roehampton | Results |
| 30 Jul 2000 | Semi-Final | Charterhouse Friars v Eton Ramblers | Charterhouse School, Godalming | Results |
| 30 Jul 2000 | Semi-Final | Old Malvernians v Old Tonbridgians | Malvern College Ground, Malvern | Results |
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