| 4 | Old Cranleighans v Felsted Robins | Jubilee, Cranleigh School | 2021 |
| 4 | Old Cranleighans v Oundle Rovers | Jubilee, Cranleigh School | 2021 |
| 3 | Old Cranleighans v Eton Ramblers | Jubilee, Cranleigh School | 2011 |
| 3 | Old Cranleighans v Rugby Meteors | Rugby School Ground, Rugby | 2013 |
| 3 | Old Cranleighans v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 2015 |
| 3 | Old Cranleighans v Old Malvernians | Arundel Castle Cricket Club Ground, Arundel | 2018 |
| 2 | Old Cranleighans v Old Malvernians | Old Deer Park, Richmond | 2008 |
| 2 | Old Cranleighans v St Edward's Martyrs | St Edward's School Ground, Oxford | 2012 |
| 2 | Old Cranleighans v Shrewsbury Saracens | Shrewsbury School, Shrewsbury | 2013 |
| 2 | Old Cranleighans v Old Tonbridgians | Church Road, Wimbledon | 2013 |
| 2 | Old Cranleighans v Old Cheltonians | Jubilee, Cranleigh School | 2014 |
| 2 | Old Cranleighans v Bradfield Waifs | Church Road, Wimbledon | 2014 |
| 2 | Old Cranleighans v Eton Ramblers | Upper Club, Eton College | 2015 |
| 2 | Old Cranleighans v Old Malvernians | Arundel Castle Cricket Club Ground, Arundel | 2016 |
| 2 | Old Cranleighans v Sherborne Pilgrims | Sherborne School, Sherborne | 2018 |
| 2 | Old Cranleighans v Old Bedfordians | Bedford School Ground, Bedford | 2018 |
| 2 | Old Cranleighans v Old Alleynians | Jubilee, Cranleigh School | 2019 |
| 2 | Old Cranleighans v Marlborough Blues | Jubilee, Cranleigh School | 2024 |
| 1 | Old Cranleighans v Harrow Wanderers | Jubilee, Cranleigh School | 2007 |
| 1 | Old Cranleighans v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 2009 |
| 1 | Old Cranleighans v Old Malvernians | Malvern College Ground, Malvern | 2010 |
| 1 | Old Cranleighans v Old Merchant Taylors | Jubilee, Cranleigh School | 2014 |
| 1 | Old Cranleighans v Haileybury Hermits | The Lowers, Cranleigh School | 2014 |
| 1 | Old Cranleighans v Harrow Wanderers | Jubilee, Cranleigh School | 2016 |
| 1 | Old Cranleighans v Old Cliftonians | Clifton College Close Ground, Clifton | 2016 |
| 1 | Old Cranleighans v Old Wellingtonians | Jubilee, Cranleigh School | 2016 |
| 1 | Old Cranleighans v Haileybury Hermits | Haileybury College Ground, Hertford | 2018 |
| 1 | Old Cranleighans v Bradfield Waifs | Jubilee, Cranleigh School | 2019 |
| 1 | Old Cranleighans v Uppingham Rovers | Jubilee, Cranleigh School | 2022 |
| 1 | Old Cranleighans v Old Wykehamists | Jubilee, Cranleigh School | 2023 |
| 1 | Old Cranleighans v Haileybury Hermits | Jubilee, Cranleigh School | 2024 |
