| 16 Jun 2019 | First Round | Old Tonbridgians v Haileybury Hermits | Tonbridge School Ground, Tonbridge | Results |
| 15 Jun 2019 | First Round | Old Amplefordians v Stowe Templars | Ampleforth College, Ampleforth | Results |
| 16 Jun 2019 | First Round | Old Cranleighans v Old Alleynians | Jubilee, Cranleigh School | Results |
| 16 Jun 2019 | First Round | Bradfield Waifs v Sherborne Pilgrims | Bradfield College, Reading | Results |
| 16 Jun 2019 | First Round | Charterhouse Friars v Old Hurst Johnians | Charterhouse School, Godalming | Results |
| 23 Jun 2019 | First Round | Eton Ramblers v Shrewsbury Saracens | Upper Club, Eton College | Results |
| 16 Jun 2019 | First Round | Old Merchant Taylors v Old Wykehamists | Merchant Taylors' School Ground, Northwood | Results |
| 16 Jun 2019 | First Round | Old Bedfordians v Old Eastbournians | Bedford School Ground, Bedford | Results |
| 16 Jun 2019 | First Round | Repton Pilgrims v Marlborough Blues | Repton School Ground, Repton | Results |
| 16 Jun 2019 | First Round | Old Cliftonians v Downside Wanderers | Clifton College Close Ground, Clifton | Results |
| 16 Jun 2019 | First Round | St Edward's Martyrs v Old Cholmeleians | St Edward's School Ground, Oxford | Results |
| 23 Jun 2019 | First Round | Old Malvernians v Old Millfieldians | Malvern College Ground, Malvern | Results |
| 16 Jun 2019 | First Round | Old Cheltonians v Oundle Rovers | College Ground, Cheltenham | Results |
| 16 Jun 2019 | First Round | Rugby Meteors v Radley Rangers | Rugby School Ground, Rugby | Results |
| 16 Jun 2019 | First Round | Uppingham Rovers v Felsted Robins | Upper Field, Uppingham School | Results |
| 16 Jun 2019 | First Round | Old Wellingtonians v Old Brightonians | Wellington College, Crowthorne | Results |
| 30 Jun 2019 | Second Round | Old Brightonians v Uppingham Rovers | Spen Cama Memorial Ground, Fulking | Results |
| 30 Jun 2019 | Second Round | Repton Pilgrims v Downside Wanderers | Repton School Ground, Repton | Results |
| 30 Jun 2019 | Second Round | St Edward's Martyrs v Old Malvernians | St Edward's School Ground, Oxford | Results |
| 30 Jun 2019 | Second Round | Oundle Rovers v Radley Rangers | Oundle School Ground, Oundle | Results |
| 30 Jun 2019 | Second Round | Old Tonbridgians v Old Amplefordians | Tonbridge School Ground, Tonbridge | Results |
| 30 Jun 2019 | Second Round | Old Cranleighans v Bradfield Waifs | Jubilee, Cranleigh School | Results |
| 30 Jun 2019 | Second Round | Charterhouse Friars v Shrewsbury Saracens | Charterhouse School, Godalming | Results |
| 30 Jun 2019 | Second Round | Old Merchant Taylors v Old Bedfordians | Merchant Taylors' School Ground, Northwood | Results |
| 14 Jul 2019 | Quarter-Final | Old Tonbridgians v Bradfield Waifs | Tonbridge School Ground, Tonbridge | Results |
| 14 Jul 2019 | Quarter-Final | Repton Pilgrims v Old Malvernians | Repton School Ground, Repton | Results |
| 14 Jul 2019 | Quarter-Final | Oundle Rovers v Old Brightonians | Oundle School Ground, Oundle | Results |
| 14 Jul 2019 | Quarter-Final | Charterhouse Friars v Old Bedfordians | Charterhouse School, Godalming | Results |
| 28 Jul 2019 | Semi-Final | Old Malvernians v Oundle Rovers | Malvern College Ground, Malvern | Results |
| 28 Jul 2019 | Semi-Final | Old Tonbridgians v Charterhouse Friars | Tonbridge School Ground, Tonbridge | Results |
| 11 Aug 2019 | Final | Old Tonbridgians v Oundle Rovers | Arundel Castle Cricket Club Ground, Arundel | Results |
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