| 15 Jun 2014 | First Round | Old Cheltonians v Old Cholmeleians | College Ground, Cheltenham | Results |
| 15 Jun 2014 | First Round | Old Cliftonians v Harrow Wanderers | Clifton College Close Ground, Clifton | Results |
| 15 Jun 2014 | First Round | Old Cranleighans v Old Merchant Taylors | Jubilee, Cranleigh School | Results |
| 15 Jun 2014 | First Round | Haileybury Hermits v Old Amplefordians | Haileybury College Ground, Hertford | Results |
| 15 Jun 2014 | First Round | Sherborne Pilgrims v Old Brightonians | Sherborne School, Sherborne | Results |
| 15 Jun 2014 | First Round | Charterhouse Friars v Old Alleynians | Charterhouse School, Godalming | Results |
| 15 Jun 2014 | First Round | Downside Wanderers v Oundle Rovers | Downside School, Stratton-on-the-Fosse | Results |
| 15 Jun 2014 | First Round | Old Whitgiftians v Radley Rangers | Whitgift School, Croydon | Results |
| 15 Jun 2014 | First Round | Uppingham Rovers v Bradfield Waifs | Upper Field, Uppingham School | Results |
| 15 Jun 2014 | First Round | Old Eastbournians v Repton Pilgrims | Eastbourne College Ground, Eastbourne | Results |
| 15 Jun 2014 | First Round | Old Malvernians v Eton Ramblers | Malvern College Ground, Malvern | Results |
| 15 Jun 2014 | First Round | Shrewsbury Saracens v Felsted Robins | Shrewsbury School, Shrewsbury | Results |
| 15 Jun 2014 | First Round | Old Wellingtonians v Old Wykehamists | Wellington College, Crowthorne | Results |
| 15 Jun 2014 | First Round | Rugby Meteors v Old Tonbridgians | Rugby School Ground, Rugby | Results |
| 15 Jun 2014 | First Round | Marlborough Blues v Stowe Templars | Marlborough College Ground, Marlborough | Results |
| 15 Jun 2014 | First Round | St Edward's Martyrs v Old Bedfordians | St Edward's School Ground, Oxford | Results |
| 29 Jun 2014 | Second Round | Oundle Rovers v Radley Rangers | Oundle School Ground, Oundle | Results |
| 29 Jun 2014 | Second Round | Old Cranleighans v Haileybury Hermits | The Lowers, Cranleigh School | Results |
| 29 Jun 2014 | Second Round | Old Cheltonians v Harrow Wanderers | College Ground, Cheltenham | Results |
| 29 Jun 2014 | Second Round | Stowe Templars v Old Bedfordians | Stowe School Ground, Stowe | Results |
| 29 Jun 2014 | Second Round | Old Wykehamists v Rugby Meteors | Ridding Field, Winchester | Results |
| 29 Jun 2014 | Second Round | Old Malvernians v Shrewsbury Saracens | Malvern College Ground, Malvern | Results |
| 29 Jun 2014 | Second Round | Bradfield Waifs v Repton Pilgrims | Bradfield College, Reading | Results |
| 29 Jun 2014 | Second Round | Sherborne Pilgrims v Charterhouse Friars | Sherborne School, Sherborne | Results |
| 13 Jul 2014 | Quarter-Final | Old Cranleighans v Old Cheltonians | Jubilee, Cranleigh School | Results |
| 13 Jul 2014 | Quarter-Final | Old Wykehamists v Stowe Templars | Ridding Field, Winchester | Results |
| 13 Jul 2014 | Quarter-Final | Bradfield Waifs v Old Malvernians | Bradfield College, Reading | Results |
| 13 Jul 2014 | Quarter-Final | Charterhouse Friars v Oundle Rovers | Charterhouse School, Godalming | Results |
| 27 Jul 2014 | Semi-Final | Bradfield Waifs v Stowe Templars | Bradfield College, Reading | Results |
| 27 Jul 2014 | Semi-Final | Old Cranleighans v Charterhouse Friars | Jubilee, Cranleigh School | Results |
| 17 Aug 2014 | Final | Bradfield Waifs v Old Cranleighans | Church Road, Wimbledon | Results |
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