| 8 | Old Wellingtonians v Oundle Rovers | Wellington College, Crowthorne | 1978 |
| 8 | Old Wellingtonians v Old Malvernians | Wellington College, Crowthorne | 1989 |
| 7 | Old Wellingtonians v Charterhouse Friars | Charterhouse School, Godalming | 1973 |
| 7 | Old Wellingtonians v Sherborne Pilgrims | Wellington College, Crowthorne | 1981 |
| 7 | Old Wellingtonians v St Edward's Martyrs | St Edward's School Ground, Oxford | 1990 |
| 7 | Old Wellingtonians v Lancing Rovers | Wellington College, Crowthorne | 2006 |
| 7 | Old Wellingtonians v Haileybury Hermits | Wellington College, Crowthorne | 2024 |
| 6 | Old Wellingtonians v Old Malvernians | Wellington College, Crowthorne | 1967 |
| 6 | Old Wellingtonians v Oundle Rovers | Wellington College, Crowthorne | 1969 |
| 6 | Old Wellingtonians v Old Merchant Taylors | Wellington College, Crowthorne | 1972 |
| 6 | Old Wellingtonians v Old Cliftonians | Clifton College Close Ground, Clifton | 1975 |
| 6 | Old Wellingtonians v Uppingham Rovers | Wellington College, Crowthorne | 1976 |
| 6 | Old Wellingtonians v Repton Pilgrims | Repton School Ground, Repton | 1976 |
| 6 | Old Wellingtonians v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 1977 |
| 6 | Old Wellingtonians v Oundle Rovers | Wellington College, Crowthorne | 1991 |
| 6 | Old Wellingtonians v Bradfield Waifs | Bradfield College, Reading | 1999 |
| 6 | Old Wellingtonians v Eton Ramblers | Upper Club, Eton College | 2009 |
| 6 | Old Wellingtonians v Charterhouse Friars | Wellington College, Crowthorne | 2016 |
| 6 | Old Wellingtonians v Rugby Meteors | Rugby School Ground, Rugby | 2018 |
| 6 | Old Wellingtonians v Old Bedfordians | Wellington College, Crowthorne | 2018 |
| 6 | Old Wellingtonians v St Edward's Martyrs | St Edward's School Ground, Oxford | 2021 |
| 6 | Old Wellingtonians v Old Eastbournians | Eastbourne College Ground, Eastbourne | 2023 |
| 6 | Old Wellingtonians v Harrow Wanderers | Wellington College, Crowthorne | 2025 |
| 5 | Old Wellingtonians v Shrewsbury Saracens | Shrewsbury School, Shrewsbury | 1968 |
| 5 | Old Wellingtonians v Charterhouse Friars | Charterhouse School, Godalming | 1968 |
| 5 | Old Wellingtonians v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 1968 |
| 5 | Old Wellingtonians v Uppingham Rovers | Upper Field, Uppingham School | 1971 |
| 5 | Old Wellingtonians v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 1984 |
| 5 | Old Wellingtonians v Eton Ramblers | Wellington College, Crowthorne | 1985 |
| 5 | Old Wellingtonians v Bradfield Waifs | Wellington College, Crowthorne | 1986 |
| 5 | Old Wellingtonians v Charterhouse Friars | Wellington College, Crowthorne | 1987 |
| 5 | Old Wellingtonians v Old Blundellians | Wellington College, Crowthorne | 1992 |
| 5 | Old Wellingtonians v Old Cliftonians | Wellington College, Crowthorne | 1994 |
| 5 | Old Wellingtonians v Old Brightonians | Wellington College, Crowthorne | 1998 |
| 5 | Old Wellingtonians v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 2001 |
| 5 | Old Wellingtonians v Eton Ramblers | Wellington College, Crowthorne | 2001 |
| 5 | Old Wellingtonians v Old Tonbridgians | Wellington College, Crowthorne | 2004 |
| 5 | Old Wellingtonians v Radley Rangers | Wellington College, Crowthorne | 2006 |
| 5 | Old Wellingtonians v Old Cheltonians | Wellington College, Crowthorne | 2008 |
| 5 | Old Wellingtonians v Stowe Templars | Stowe School Ground, Stowe | 2011 |
| 5 | Old Wellingtonians v Old Wykehamists | Wellington College, Crowthorne | 2012 |
| 5 | Old Wellingtonians v Eton Ramblers | Upper Club, Eton College | 2015 |
| 5 | Old Wellingtonians v Stowe Templars | Wellington College, Crowthorne | 2016 |
| 5 | Old Wellingtonians v Old Malvernians | Wellington College, Crowthorne | 2017 |
| 5 | Old Wellingtonians v Old Brightonians | Wellington College, Crowthorne | 2019 |
