| 03 Jun 1990 | First Round | Old Merchant Taylors v Sherborne Pilgrims | Durrants Sports Ground, Croxley Green | Results |
| 10 Jun 1990 | First Round (replay) | Sherborne Pilgrims v Old Merchant Taylors | Sherborne School, Sherborne | Results |
| 24 Jun 1990 | Second Round | Old Malvernians v Sherborne Pilgrims | Malvern College Ground, Malvern | Results |
| 03 Jun 1990 | First Round | St Edward's Martyrs v Old Wellingtonians | St Edward's School Ground, Oxford | Results |
| 03 Jun 1990 | First Round | Repton Pilgrims v Shrewsbury Saracens | Repton School Ground, Repton | Results |
| 03 Jun 1990 | First Round | Uppingham Rovers v Old Westminsters | Middle Field Pitch 1, Uppingham School | Results |
| 03 Jun 1990 | First Round | Old Blundellians v Rugby Meteors | Blundell's School, Tiverton | Results |
| 03 Jun 1990 | First Round | Old Malvernians v Old Wykehamists | Malvern College Ground, Malvern | Results |
| 03 Jun 1990 | First Round | Radley Rangers v Oundle Rovers | Radley College Bigside Ground, Abingdon | Results |
| 03 Jun 1990 | First Round | Stowe Templars v Bradfield Waifs | Stowe School Ground, Stowe | Results |
| 03 Jun 1990 | First Round | Old Cliftonians v Marlborough Blues | Clifton College Close Ground, Clifton | Results |
| 03 Jun 1990 | First Round | Old Whitgiftians v Old Alleynians | Croham Manor Road, Croydon | Results |
| 03 Jun 1990 | First Round | Eton Ramblers v Old Cholmeleians | Upper Club, Eton College | Results |
| 03 Jun 1990 | First Round | Harrow Wanderers v Old Cheltonians | Harrow School Cricket Ground, Harrow-on-the-Hill | Results |
| 03 Jun 1990 | First Round | Downside Wanderers v Old Amplefordians | Downside School, Stratton-on-the-Fosse | Results |
| 03 Jun 1990 | First Round | Lancing Rovers v Charterhouse Friars | Lancing College Ground, Lancing | Results |
| 10 Jun 1990 | First Round | Old Tonbridgians v Felsted Robins | Tonbridge School Ground, Tonbridge | Results |
| 10 Jun 1990 | First Round | Haileybury Hermits v Old Brightonians | Haileybury College Ground, Hertford | Results |
| 24 Jun 1990 | Second Round | St Edward's Martyrs v Shrewsbury Saracens | St Edward's School Ground, Oxford | Results |
| 24 Jun 1990 | Second Round | Uppingham Rovers v Rugby Meteors | Middle Field Pitch 1, Uppingham School | Results |
| 24 Jun 1990 | Second Round | Haileybury Hermits v Oundle Rovers | Haileybury College Ground, Hertford | Results |
| 24 Jun 1990 | Second Round | Bradfield Waifs v Old Cliftonians | Bradfield College, Reading | Results |
| 24 Jun 1990 | Second Round | Old Alleynians v Eton Ramblers | Dulwich College Ground, Dulwich | Results |
| 24 Jun 1990 | Second Round | Old Tonbridgians v Harrow Wanderers | Tonbridge School Ground, Tonbridge | Results |
| 01 Jul 1990 | Second Round | Charterhouse Friars v Downside Wanderers | Charterhouse School, Godalming | Results |
| 08 Jul 1990 | Quarter-Final | Shrewsbury Saracens v Rugby Meteors | Shrewsbury School, Shrewsbury | Results |
| 08 Jul 1990 | Quarter-Final | Old Malvernians v Oundle Rovers | Malvern College Ground, Malvern | Results |
| 08 Jul 1990 | Quarter-Final | Old Cliftonians v Eton Ramblers | Clifton College Close Ground, Clifton | Results |
| 08 Jul 1990 | Quarter-Final | Harrow Wanderers v Downside Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | Results |
| 22 Jul 1990 | Semi-Final | Rugby Meteors v Old Malvernians | Rugby School Ground, Rugby | Results |
| 23 Jul 1990 | Semi-Final | Old Cliftonians v Harrow Wanderers | Clifton College Close Ground, Clifton | Results |
| 05 Aug 1990 | Final | Harrow Wanderers v Old Malvernians | Vincent Square, Westminster | Results |
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