| 4 | Old Wellingtonians v Old Malvernians | Malvern College Ground, Malvern | 2005 |
| 3 | Old Wellingtonians v Uppingham Rovers | Middle Field Pitch 1, Uppingham School | 1987 |
| 3 | Old Wellingtonians v Old Cliftonians | Wellington College, Crowthorne | 1994 |
| 3 | Old Wellingtonians v Uppingham Rovers | Wellington College, Crowthorne | 1996 |
| 3 | Old Wellingtonians v Oundle Rovers | Oundle School Ground, Oundle | 2007 |
| 3 | Old Wellingtonians v Rugby Meteors | Rugby School Ground, Rugby | 2013 |
| 3 | Old Wellingtonians v Old Wykehamists | Wellington College, Crowthorne | 2014 |
| 3 | Old Wellingtonians v Old Eastbournians | Eastbourne College Ground, Eastbourne | 2023 |
| 2 | Old Wellingtonians v Repton Pilgrims | Repton School Ground, Repton | 1976 |
| 2 | Old Wellingtonians v Eton Ramblers | Wellington College, Crowthorne | 1985 |
| 2 | Old Wellingtonians v Sherborne Pilgrims | Wellington College, Crowthorne | 1991 |
| 2 | Old Wellingtonians v Oundle Rovers | Wellington College, Crowthorne | 1991 |
| 2 | Old Wellingtonians v Bradfield Waifs | Bradfield College, Reading | 1999 |
| 2 | Old Wellingtonians v Old Cheltonians | Wellington College, Crowthorne | 2002 |
| 2 | Old Wellingtonians v Old Tonbridgians | Wellington College, Crowthorne | 2004 |
| 2 | Old Wellingtonians v Lancing Rovers | Wellington College, Crowthorne | 2006 |
| 2 | Old Wellingtonians v Old Cheltonians | Wellington College, Crowthorne | 2008 |
| 2 | Old Wellingtonians v Old Wykehamists | Wellington College, Crowthorne | 2012 |
| 2 | Old Wellingtonians v Radley Rangers | Wellington College, Crowthorne | 2013 |
| 2 | Old Wellingtonians v Eton Ramblers | Upper Club, Eton College | 2015 |
| 2 | Old Wellingtonians v Bradfield Waifs | Bradfield College, Reading | 2017 |
| 2 | Old Wellingtonians v Old Malvernians | Wellington College, Crowthorne | 2017 |
| 2 | Old Wellingtonians v Old Eastbournians | Arundel Castle Cricket Club Ground, Arundel | 2017 |
| 2 | Old Wellingtonians v St Edward's Martyrs | St Edward's School Ground, Oxford | 2021 |
| 2 | Old Wellingtonians v Old Hurst Johnians | Wellington College, Crowthorne | 2022 |
| 2 | Old Wellingtonians v Oundle Rovers | Oundle School Ground, Oundle | 2023 |
| 1 | Old Wellingtonians v Old Malvernians | Wellington College, Crowthorne | 1967 |
| 1 | Old Wellingtonians v Shrewsbury Saracens | Shrewsbury School, Shrewsbury | 1968 |
| 1 | Old Wellingtonians v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 1968 |
| 1 | Old Wellingtonians v Oundle Rovers | Oundle School Ground, Oundle | 1970 |
| 1 | Old Wellingtonians v Charterhouse Friars | Charterhouse School, Godalming | 1973 |
| 1 | Old Wellingtonians v Sherborne Pilgrims | Wellington College, Crowthorne | 1981 |
| 1 | Old Wellingtonians v Repton Pilgrims | Wellington College, Crowthorne | 1983 |
| 1 | Old Wellingtonians v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 1985 |
| 1 | Old Wellingtonians v Charterhouse Friars | Charterhouse School, Godalming | 1986 |
| 1 | Old Wellingtonians v Marlborough Blues | Marlborough College Ground, Marlborough | 1992 |
| 1 | Old Wellingtonians v Old Cliftonians | Wellington College, Crowthorne | 1995 |
| 1 | Old Wellingtonians v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 1995 |
| 1 | Old Wellingtonians v Old Malvernians | Bank of England Ground, Roehampton | 1995 |
| 1 | Old Wellingtonians v Old Merchant Taylors | Wellington College, Crowthorne | 1997 |
| 1 | Old Wellingtonians v Old Brightonians | Wellington College, Crowthorne | 1998 |
| 1 | Old Wellingtonians v Old Amplefordians | Wellington College, Crowthorne | 1999 |
| 1 | Old Wellingtonians v Old Brightonians | Wellington College, Crowthorne | 2000 |
| 1 | Old Wellingtonians v Eton Ramblers | Wellington College, Crowthorne | 2000 |
| 1 | Old Wellingtonians v Uppingham Rovers | Wellington College, Crowthorne | 2001 |
| 1 | Old Wellingtonians v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 2001 |
| 1 | Old Wellingtonians v Eton Ramblers | Upper Club, Eton College | 2002 |
| 1 | Old Wellingtonians v Sherborne Pilgrims | Sherborne School, Sherborne | 2002 |
| 1 | Old Wellingtonians v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 2002 |
| 1 | Old Wellingtonians v Radley Rangers | Wellington College, Crowthorne | 2006 |
| 1 | Old Wellingtonians v Old Cholmeleians | Highgate School Ground, Highgate | 2007 |
| 1 | Old Wellingtonians v Old Cholmeleians | Wellington College, Crowthorne | 2010 |
| 1 | Old Wellingtonians v Old Whitgiftians | Whitgift School, Croydon | 2010 |
| 1 | Old Wellingtonians v Eton Ramblers | Wellington College, Crowthorne | 2011 |
| 1 | Old Wellingtonians v Old Eastbournians | Eastbourne College Ground, Eastbourne | 2012 |
| 1 | Old Wellingtonians v Charterhouse Friars | Wellington College, Crowthorne | 2016 |
| 1 | Old Wellingtonians v Rugby Meteors | Rugby School Ground, Rugby | 2017 |
| 1 | Old Wellingtonians v Charterhouse Friars | Wellington College, Crowthorne | 2017 |
| 1 | Old Wellingtonians v Old Amplefordians | Wellington College, Crowthorne | 2018 |
| 1 | Old Wellingtonians v Old Cranleighans | Wellington College, Crowthorne | 2022 |
| 1 | Old Wellingtonians v Old Hamptonians | Hampton School, Hampton | 2024 |
| 1 | Old Wellingtonians v Harrow Wanderers | Wellington College, Crowthorne | 2025 |
