| 04 Jun 1989 | First Round | Bradfield Waifs v Sherborne Pilgrims | Bradfield College, Reading | Results |
| 04 Jun 1989 | First Round | Old Westminsters v Old Cliftonians | Vincent Square, Westminster | Results |
| 04 Jun 1989 | First Round | Oundle Rovers v Old Brightonians | Oundle School Ground, Oundle | Results |
| 04 Jun 1989 | First Round | Charterhouse Friars v Eton Ramblers | Charterhouse School, Godalming | Results |
| 04 Jun 1989 | First Round | Old Wellingtonians v Old Cheltonians | Wellington College, Crowthorne | Results |
| 04 Jun 1989 | First Round | Old Malvernians v Old Amplefordians | Malvern College Ground, Malvern | Results |
| 04 Jun 1989 | First Round | Old Cholmeleians v Repton Pilgrims | Highgate School Ground, Highgate | Results |
| 04 Jun 1989 | First Round | Old Alleynians v Stowe Templars | Dulwich College Ground, Dulwich | Results |
| 04 Jun 1989 | First Round | Old Whitgiftians v Harrow Wanderers | Whitgift School, Croydon | Results |
| 04 Jun 1989 | First Round | Marlborough Blues v Felsted Robins | Marlborough College Ground, Marlborough | Results |
| 04 Jun 1989 | First Round | Rugby Meteors v Downside Wanderers | Rugby School Ground, Rugby | Results |
| 04 Jun 1989 | First Round | Old Tonbridgians v Uppingham Rovers | Tonbridge School Ground, Tonbridge | Results |
| 04 Jun 1989 | First Round | Old Wykehamists v Radley Rangers | Ridding Field, Winchester | Results |
| 04 Jun 1989 | First Round | St Edward's Martyrs v Haileybury Hermits | St Edward's School Ground, Oxford | Results |
| 04 Jun 1989 | First Round | Old Blundellians v Lancing Rovers | Blundell's School, Tiverton | Results |
| 04 Jun 1989 | First Round | Shrewsbury Saracens v Old Merchant Taylors | Shrewsbury School, Shrewsbury | Results |
| 25 Jun 1989 | Second Round | Bradfield Waifs v Old Cliftonians | Bradfield College, Reading | Results |
| 25 Jun 1989 | Second Round | Oundle Rovers v Eton Ramblers | Oundle School Ground, Oundle | Results |
| 25 Jun 1989 | Second Round | Old Wellingtonians v Old Malvernians | Wellington College, Crowthorne | Results |
| 25 Jun 1989 | Second Round | Repton Pilgrims v Old Alleynians | Repton School Ground, Repton | Results |
| 25 Jun 1989 | Second Round | Harrow Wanderers v Marlborough Blues | Harrow School Cricket Ground, Harrow-on-the-Hill | Results |
| 25 Jun 1989 | Second Round | Downside Wanderers v Old Tonbridgians | Downside School, Stratton-on-the-Fosse | Results |
| 25 Jun 1989 | Second Round | Radley Rangers v St Edward's Martyrs | Radley College Bigside Ground, Abingdon | Results |
| 25 Jun 1989 | Second Round | Old Blundellians v Shrewsbury Saracens | Blundell's School, Tiverton | Results |
| 09 Jul 1989 | Quarter-Final | Old Cliftonians v Oundle Rovers | Clifton College Close Ground, Clifton | Results |
| 09 Jul 1989 | Quarter-Final | Old Malvernians v Repton Pilgrims | Malvern College Ground, Malvern | Results |
| 09 Jul 1989 | Quarter-Final | Marlborough Blues v Old Tonbridgians | Marlborough College Ground, Marlborough | Results |
| 09 Jul 1989 | Quarter-Final | St Edward's Martyrs v Shrewsbury Saracens | St Edward's School Ground, Oxford | Results |
| 23 Jul 1989 | Semi-Final | Oundle Rovers v Old Malvernians | Oundle School Ground, Oundle | Results |
| 23 Jul 1989 | Semi-Final | Marlborough Blues v Shrewsbury Saracens | Marlborough College Ground, Marlborough | Results |
| 06 Aug 1989 | Final | Oundle Rovers v Shrewsbury Saracens | Vincent Square, Westminster | Results |
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