| 25 May 1969 | First Round | Stowe Templars v Radley Rangers | Stowe School Ground, Stowe | Results |
| 25 May 1969 | First Round | Old Cheltonians v Old Cholmeleians | College Ground, Cheltenham | Results |
| 25 May 1969 | First Round | Bradfield Waifs v Old Merchant Taylors | Bradfield College, Reading | Results |
| 25 May 1969 | First Round | Lancing Rovers v Old Alleynians | Lancing College Ground, Lancing | Results |
| 25 May 1969 | First Round | Harrow Wanderers v St Edward's Martyrs | Harrow School Cricket Ground, Harrow-on-the-Hill | Results |
| 25 May 1969 | First Round | Old Amplefordians v Old Cliftonians | Ampleforth College, Ampleforth | Results |
| 25 May 1969 | First Round | Uppingham Rovers v Old Whitgiftians | Upper Field, Uppingham School | Results |
| 25 May 1969 | First Round | Eton Ramblers v Repton Pilgrims | Agar's Plough, Eton College | Results |
| 25 May 1969 | First Round | Old Tonbridgians v Old Brightonians | Tonbridge School Ground, Tonbridge | Results |
| 25 May 1969 | First Round | Felsted Robins v Charterhouse Friars | Felsted School Ground, Dunmow | Results |
| 25 May 1969 | First Round | Old Blundellians v Shrewsbury Saracens | Blundell's School, Tiverton | Results |
| 25 May 1969 | First Round | Rugby Meteors v Sherborne Pilgrims | Rugby School Ground, Rugby | Results |
| 25 May 1969 | First Round | Haileybury Hermits v Old Westminsters | Haileybury College Ground, Hertford | Results |
| 25 May 1969 | First Round | Old Wykehamists v Downside Wanderers | Ridding Field, Winchester | Results |
| 25 May 1969 | First Round | Old Malvernians v Marlborough Blues | Malvern College Ground, Malvern | Results |
| 25 May 1969 | First Round | Old Wellingtonians v Oundle Rovers | Wellington College, Crowthorne | Results |
| 15 Jun 1969 | Second Round | Stowe Templars v Old Cholmeleians | Stowe School Ground, Stowe | Results |
| 15 Jun 1969 | Second Round | Old Merchant Taylors v Old Alleynians | Durrants Sports Ground, Croxley Green | Results |
| 15 Jun 1969 | Second Round | Harrow Wanderers v Old Amplefordians | Harrow School Cricket Ground, Harrow-on-the-Hill | Results |
| 15 Jun 1969 | Second Round | Old Brightonians v Felsted Robins | Brighton College Ground, Brighton | Results |
| 15 Jun 1969 | Second Round | Shrewsbury Saracens v Rugby Meteors | Shrewsbury School, Shrewsbury | Results |
| 15 Jun 1969 | Second Round | Haileybury Hermits v Old Wykehamists | Haileybury College Ground, Hertford | Results |
| 15 Jun 1969 | Second Round | Old Malvernians v Oundle Rovers | Malvern College Ground, Malvern | Results |
| 15 Jun 1969 | Second Round | Uppingham Rovers v Eton Ramblers | Upper Field, Uppingham School | Results |
| 06 Jul 1969 | Quarter-Final | Stowe Templars v Old Merchant Taylors | Stowe School Ground, Stowe | Results |
| 06 Jul 1969 | Quarter-Final | Old Amplefordians v Uppingham Rovers | Ampleforth College, Ampleforth | Results |
| 06 Jul 1969 | Quarter-Final | Old Malvernians v Haileybury Hermits | Malvern College Ground, Malvern | Results |
| 06 Jul 1969 | Quarter-Final | Old Brightonians v Rugby Meteors | Brighton College Ground, Brighton | Results |
| 13 Jul 1969 | Quarter-Final (replay) | Old Malvernians v Haileybury Hermits | Malvern College Ground, Malvern | Results |
| 13 Jul 1969 | Quarter-Final (replay) | Rugby Meteors v Old Brightonians | Rugby School Ground, Rugby | Results |
| 27 Jul 1969 | Semi-Final | Stowe Templars v Uppingham Rovers | Stowe School Ground, Stowe | Results |
| 27 Jul 1969 | Semi-Final | Old Brightonians v Old Malvernians | Brighton College Ground, Brighton | Results |
| 24 Aug 1969 | Final | Old Brightonians v Stowe Templars | Burton's Court, Chelsea | Results |
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