| 19 Jun 2016 | First Round | Repton Pilgrims v Old Amplefordians | Repton School Ground, Repton | Results |
| 12 Jun 2016 | First Round | Old Malvernians v Oundle Rovers | Malvern College Ground, Malvern | Results |
| 12 Jun 2016 | First Round | Old Alleynians v Eton Ramblers | Dulwich College Ground, Dulwich | Results |
| 12 Jun 2016 | First Round | Felsted Robins v Shrewsbury Saracens | Felsted School Ground, Dunmow | Results |
| 12 Jun 2016 | First Round | Old Tonbridgians v Old Cheltonians | Tonbridge School Ground, Tonbridge | Results |
| 12 Jun 2016 | First Round | Old Eastbournians v Haileybury Hermits | Eastbourne College Ground, Eastbourne | Results |
| 12 Jun 2016 | First Round | Old Merchant Taylors v Bradfield Waifs | Merchant Taylors' School Ground, Northwood | Results |
| 12 Jun 2016 | First Round | Rugby Meteors v Marlborough Blues | Rugby School Ground, Rugby | Results |
| 12 Jun 2016 | First Round | Uppingham Rovers v Sherborne Pilgrims | Upper Field, Uppingham School | Results |
| 12 Jun 2016 | First Round | Old Wykehamists v Old Whitgiftians | Ridding Field, Winchester | Results |
| 19 Jun 2016 | First Round | St Edward's Martyrs v Old Cliftonians | St Edward's School Ground, Oxford | Results |
| 12 Jun 2016 | First Round | Old Cranleighans v Harrow Wanderers | Jubilee, Cranleigh School | Results |
| 19 Jun 2016 | First Round | Old Wellingtonians v Stowe Templars | Wellington College, Crowthorne | Results |
| 12 Jun 2016 | First Round | Radley Rangers v Old Bedfordians | Radley College Bigside Ground, Abingdon | Results |
| 12 Jun 2016 | First Round | Old Brightonians v Charterhouse Friars | Brighton College Ground, Brighton | Results |
| 12 Jun 2016 | First Round | Old Cholmeleians v Downside Wanderers | Tivoli Road, Hornsey | Results |
| 03 Jul 2016 | Second Round | Rugby Meteors v Bradfield Waifs | Rugby School Ground, Rugby | Results |
| 26 Jun 2016 | Second Round | Old Cliftonians v Old Cranleighans | Clifton College Close Ground, Clifton | Results |
| 26 Jun 2016 | Second Round | Old Wellingtonians v Radley Rangers | Wellington College, Crowthorne | Results |
| 26 Jun 2016 | Second Round | Charterhouse Friars v Downside Wanderers | Charterhouse School, Godalming | Results |
| 03 Jul 2016 | Second Round | Old Malvernians v Repton Pilgrims | Malvern College Ground, Malvern | Results |
| 26 Jun 2016 | Second Round | Old Alleynians v Shrewsbury Saracens | Dulwich College Trevor Bailey Sports Ground, Dulwich Common | Results |
| 26 Jun 2016 | Second Round | Old Tonbridgians v Old Eastbournians | Tonbridge School Ground, Tonbridge | Results |
| 26 Jun 2016 | Second Round | Uppingham Rovers v Old Wykehamists | Upper Field, Uppingham School | Results |
| 10 Jul 2016 | Quarter-Final | Old Tonbridgians v Bradfield Waifs | Tonbridge School Ground, Tonbridge | Results |
| 10 Jul 2016 | Quarter-Final | Old Wellingtonians v Charterhouse Friars | Wellington College, Crowthorne | Results |
| 10 Jul 2016 | Quarter-Final | Old Wykehamists v Old Cranleighans | Ridding Field, Winchester | Results |
| 10 Jul 2016 | Quarter-Final | Old Malvernians v Old Alleynians | Malvern College Ground, Malvern | Results |
| 24 Jul 2016 | Semi-Final | Old Cranleighans v Old Wellingtonians | Jubilee, Cranleigh School | Results |
| 24 Jul 2016 | Semi-Final | Old Malvernians v Old Tonbridgians | Malvern College Ground, Malvern | Results |
| 07 Aug 2016 | Final | Old Cranleighans v Old Malvernians | Arundel Castle Cricket Club Ground, Arundel | Results |
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