| 01 Jun 1986 | First Round | Sherborne Pilgrims v Downside Wanderers | Sherborne School, Sherborne | Results |
| 01 Jun 1986 | First Round | Harrow Wanderers v Repton Pilgrims | Harrow School Cricket Ground, Harrow-on-the-Hill | Results |
| 01 Jun 1986 | First Round | Old Wykehamists v Old Cheltonians | Ridding Field, Winchester | Results |
| 01 Jun 1986 | First Round | Marlborough Blues v Old Whitgiftians | Marlborough College Ground, Marlborough | Results |
| 01 Jun 1986 | First Round | Old Brightonians v Haileybury Hermits | Brighton College Ground, Brighton | Results |
| 01 Jun 1986 | First Round | Uppingham Rovers v Old Cholmeleians | Upper Field, Uppingham School | Results |
| 01 Jun 1986 | First Round | Old Westminsters v Felsted Robins | Vincent Square, Westminster | Results |
| 01 Jun 1986 | First Round | Lancing Rovers v St Edward's Martyrs | Lancing College Ground, Lancing | Results |
| 01 Jun 1986 | First Round | Eton Ramblers v Old Amplefordians | Upper Club, Eton College | Results |
| 01 Jun 1986 | First Round | Shrewsbury Saracens v Rugby Meteors | Shrewsbury School, Shrewsbury | Results |
| 01 Jun 1986 | First Round | Old Cliftonians v Stowe Templars | Clifton College Close Ground, Clifton | Results |
| 01 Jun 1986 | First Round | Oundle Rovers v Old Blundellians | Oundle School Ground, Oundle | Results |
| 01 Jun 1986 | First Round | Old Merchant Taylors v Old Malvernians | Durrants Sports Ground, Croxley Green | Results |
| 01 Jun 1986 | First Round | Old Alleynians v Old Tonbridgians | Old Alleynians Ground, Dulwich Common | Results |
| 01 Jun 1986 | First Round | Old Wellingtonians v Bradfield Waifs | Wellington College, Crowthorne | Results |
| 01 Jun 1986 | First Round | Radley Rangers v Charterhouse Friars | Radley College Bigside Ground, Abingdon | Results |
| 22 Jun 1986 | Second Round | Repton Pilgrims v Old Wykehamists | Repton School Ground, Repton | Results |
| 22 Jun 1986 | Second Round | Marlborough Blues v Old Brightonians | Marlborough College Ground, Marlborough | Results |
| 22 Jun 1986 | Second Round | Felsted Robins v Old Cholmeleians | Felsted School Ground, Dunmow | Results |
| 22 Jun 1986 | Second Round | Lancing Rovers v Downside Wanderers | Lancing College Ground, Lancing | Results |
| 22 Jun 1986 | Second Round | Eton Ramblers v Shrewsbury Saracens | Upper Club, Eton College | Results |
| 22 Jun 1986 | Second Round | Old Cliftonians v Oundle Rovers | Clifton College Close Ground, Clifton | Results |
| 22 Jun 1986 | Second Round | Old Malvernians v Old Tonbridgians | Malvern College Ground, Malvern | Results |
| 29 Jun 1986 | Second Round | Charterhouse Friars v Old Wellingtonians | Charterhouse School, Godalming | Results |
| 06 Jul 1986 | Quarter-Final | Old Wykehamists v Marlborough Blues | Ridding Field, Winchester | Results |
| 06 Jul 1986 | Quarter-Final | Felsted Robins v Downside Wanderers | Felsted School Ground, Dunmow | Results |
| 06 Jul 1986 | Quarter-Final | Shrewsbury Saracens v Oundle Rovers | Shrewsbury School, Shrewsbury | Results |
| 06 Jul 1986 | Quarter-Final | Old Malvernians v Charterhouse Friars | Malvern College Ground, Malvern | Results |
| 20 Jul 1986 | Semi-Final | Marlborough Blues v Downside Wanderers | Marlborough College Ground, Marlborough | Results |
| 20 Jul 1986 | Semi-Final | Oundle Rovers v Old Malvernians | Oundle School Ground, Oundle | Results |
| 10 Aug 1986 | Final | Downside Wanderers v Old Malvernians | Vincent Square, Westminster | Results |
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