| 30 May 1999 | First Round | Sherborne Pilgrims v St Edward's Martyrs | Sherborne School, Sherborne | Results |
| 20 Jun 1999 | Second Round | Sherborne Pilgrims v Old Merchant Taylors | Sherborne School, Sherborne | Results |
| 04 Jul 1999 | Quarter-Final | Radley Rangers v Sherborne Pilgrims | Radley College Bigside Ground, Abingdon | Results |
| 18 Jul 1999 | Semi-Final | Sherborne Pilgrims v Bradfield Waifs | Sherborne School, Sherborne | Results |
| 30 May 1999 | First Round | Old Tonbridgians v Old Whitgiftians | Tonbridge School Ground, Tonbridge | Results |
| 30 May 1999 | First Round | Old Brightonians v Old Cheltonians | Brighton College Ground, Brighton | Results |
| 06 Jun 1999 | First Round | Oundle Rovers v Harrow Wanderers | Oundle School Ground, Oundle | Results |
| 30 May 1999 | First Round | Haileybury Hermits v Stowe Templars | Haileybury College Ground, Hertford | Results |
| 06 Jun 1999 | First Round | Felsted Robins v Rugby Meteors | Felsted School Ground, Dunmow | Results |
| 30 May 1999 | First Round | Eton Ramblers v Shrewsbury Saracens | Upper Club, Eton College | Results |
| 30 May 1999 | First Round | Old Westminsters v Old Alleynians | Vincent Square, Westminster | Results |
| 30 May 1999 | First Round | Lancing Rovers v Old Cliftonians | Lancing College Ground, Lancing | Results |
| 30 May 1999 | First Round | Radley Rangers v Downside Wanderers | Radley College Bigside Ground, Abingdon | Results |
| 31 May 1999 | First Round | Old Wykehamists v Marlborough Blues | Ridding Field, Winchester | Results |
| 30 May 1999 | First Round | Old Cholmeleians v Old Merchant Taylors | Highgate School Ground, Highgate | Results |
| 30 May 1999 | First Round | Old Blundellians v Bradfield Waifs | Blundell's School, Tiverton | Results |
| 30 May 1999 | First Round | Old Malvernians v Charterhouse Friars | Malvern College Ground, Malvern | Results |
| 30 May 1999 | First Round | Old Wellingtonians v Repton Pilgrims | Wellington College, Crowthorne | Results |
| 06 Jun 1999 | First Round (replay) | Haileybury Hermits v Stowe Templars | Haileybury College Ground, Hertford | Results |
| 13 Jun 1999 | First Round (Replay) | Uppingham Rovers v Old Amplefordians | Middle Field Pitch 1, Uppingham School | Results |
| 20 Jun 1999 | Second Round | Old Tonbridgians v Old Brightonians | Tonbridge School Ground, Tonbridge | Results |
| 20 Jun 1999 | Second Round | Oundle Rovers v Stowe Templars | Oundle School Ground, Oundle | Results |
| 20 Jun 1999 | Second Round | Felsted Robins v Eton Ramblers | Felsted School Ground, Dunmow | Results |
| 20 Jun 1999 | Second Round | Old Alleynians v Lancing Rovers | Dulwich College Ground, Dulwich | Results |
| 13 Jun 1999 | Second Round | Radley Rangers v Old Wykehamists | Radley College Bigside Ground, Abingdon | Results |
| 20 Jun 1999 | Second Round | Bradfield Waifs v Old Malvernians | Bradfield College, Reading | Results |
| 20 Jun 1999 | Second Round | Old Wellingtonians v Old Amplefordians | Wellington College, Crowthorne | Results |
| 04 Jul 1999 | Quarter-Final | Old Tonbridgians v Oundle Rovers | Tonbridge School Ground, Tonbridge | Results |
| 04 Jul 1999 | Quarter-Final | Eton Ramblers v Old Alleynians | Agar's Plough, Eton College | Results |
| 04 Jul 1999 | Quarter-Final | Bradfield Waifs v Old Wellingtonians | Bradfield College, Reading | Results |
| 18 Jul 1999 | Semi-Final | Old Tonbridgians v Old Alleynians | Tonbridge School Ground, Tonbridge | Results |
| 15 Aug 1999 | Final | Bradfield Waifs v Old Tonbridgians | Bank of England Ground, Roehampton | Results |
| 06 Jun 1999 | First Round | Old Amplefordians v Uppingham Rovers | Ampleforth College, Ampleforth | Results |
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