| 14 May 2023 | Preliminary Round | Old Cheltonians v Haileybury Hermits | College Ground, Cheltenham | Results |
| 28 May 2023 | Preliminary Round | Old Cranleighans v Old Wykehamists | Jubilee, Cranleigh School | Results |
| 11 Jun 2023 | First Round | Bradfield Waifs v Harrow Wanderers | Bradfield College, Reading | Results |
| 11 Jun 2023 | First Round | Stowe Templars v Felsted Robins | Stowe School Ground, Stowe | Results |
| 11 Jun 2023 | First Round | Old Tonbridgians v Old Merchant Taylors | Tonbridge School Ground, Tonbridge | Results |
| 11 Jun 2023 | First Round | Old Bedfordians v Lancing Rovers | Bedford School Ground, Bedford | Results |
| 11 Jun 2023 | First Round | Old Millfieldians v Charterhouse Friars | Millfield School, Street | Results |
| 11 Jun 2023 | First Round | Old Cheltonians v Marlborough Blues | College Ground, Cheltenham | Results |
| 11 Jun 2023 | First Round | Eton Ramblers v Old Alleynians | Upper Club, Eton College | Results |
| 11 Jun 2023 | First Round | Sherborne Pilgrims v Shrewsbury Saracens | Sherborne School, Sherborne | Results |
| 11 Jun 2023 | First Round | Rugby Meteors v Uppingham Rovers | Rugby School Ground, Rugby | Results |
| 11 Jun 2023 | First Round | Old Cliftonians v Old Amplefordians | Clifton College Close Ground, Clifton | Results |
| 11 Jun 2023 | First Round | Old Malvernians v Old Hurst Johnians | Malvern College Ground, Malvern | Results |
| 11 Jun 2023 | First Round | Old Wykehamists v Downside Wanderers | Ridding Field, Winchester | Results |
| 11 Jun 2023 | First Round | Oundle Rovers v Radley Rangers | Oundle School Ground, Oundle | Results |
| 11 Jun 2023 | First Round | St Edward's Martyrs v Old Cholmeleians | St Edward's School Ground, Oxford | Results |
| 11 Jun 2023 | First Round | Old Eastbournians v Old Wellingtonians | Eastbourne College Ground, Eastbourne | Results |
| 11 Jun 2023 | First Round | Repton Pilgrims v Old Brightonians | Repton School Ground, Repton | Results |
| 25 Jun 2023 | Second Round | Old Tonbridgians v Old Bedfordians | Tonbridge School Ground, Tonbridge | Results |
| 25 Jun 2023 | Second Round | Uppingham Rovers v Old Cliftonians | Upper Field, Uppingham School | Results |
| 25 Jun 2023 | Second Round | Bradfield Waifs v Stowe Templars | Bradfield College, Reading | Results |
| 25 Jun 2023 | Second Round | Old Malvernians v Old Wykehamists | Malvern College Ground, Malvern | Results |
| 25 Jun 2023 | Second Round | Oundle Rovers v St Edward's Martyrs | Oundle School Ground, Oundle | Results |
| 25 Jun 2023 | Second Round | Old Wellingtonians v Repton Pilgrims | Wellington College, Crowthorne | Results |
| 25 Jun 2023 | Second Round | Eton Ramblers v Shrewsbury Saracens | Upper Club, Eton College | Results |
| 25 Jun 2023 | Second Round | Old Millfieldians v Old Cheltonians | Millfield School, Street | Results |
| 09 Jul 2023 | Quarter-Final | Old Millfieldians v Eton Ramblers | Millfield School, Street | Results |
| 09 Jul 2023 | Quarter-Final | Bradfield Waifs v Old Tonbridgians | Bradfield College, Reading | Results |
| 09 Jul 2023 | Quarter-Final | Old Cliftonians v Old Malvernians | Clifton College Close Ground, Clifton | Results |
| 09 Jul 2023 | Quarter-Final | Oundle Rovers v Old Wellingtonians | Oundle School Ground, Oundle | Results |
| 23 Jul 2023 | Semi-Final | Old Malvernians v Oundle Rovers | Malvern College Ground, Malvern | Results |
| 23 Jul 2023 | Semi-Final | Old Tonbridgians v Eton Ramblers | Tonbridge School Ground, Tonbridge | Results |
| 13 Aug 2023 | Final | Old Malvernians v Old Tonbridgians | Arundel Castle Cricket Club Ground, Arundel | Results |
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