| 6 | Old Wellingtonians v Old Merchant Taylors | Durrants Sports Ground, Croxley Green | 1993 |
| 5 | Old Wellingtonians v Uppingham Rovers | Upper Field, Uppingham School | 1971 |
| 5 | Old Wellingtonians v Repton Pilgrims | Wellington College, Crowthorne | 1983 |
| 5 | Old Wellingtonians v Marlborough Blues | Marlborough College Ground, Marlborough | 1992 |
| 5 | Old Wellingtonians v Eton Ramblers | Upper Club, Eton College | 2003 |
| 5 | Old Wellingtonians v Old Malvernians | Malvern College Ground, Malvern | 2010 |
| 5 | Old Wellingtonians v Old Wykehamists | Wellington College, Crowthorne | 2014 |
| 5 | Old Wellingtonians v Bradfield Waifs | Bradfield College, Reading | 2017 |
| 5 | Old Wellingtonians v Old Brightonians | Wellington College, Crowthorne | 2019 |
| 4 | Old Wellingtonians v Oundle Rovers | Oundle School Ground, Oundle | 1970 |
| 4 | Old Wellingtonians v Old Merchant Taylors | Wellington College, Crowthorne | 1972 |
| 4 | Old Wellingtonians v Marlborough Blues | Burton's Court, Chelsea | 1980 |
| 4 | Old Wellingtonians v Eton Ramblers | Wellington College, Crowthorne | 2011 |
| 4 | Old Wellingtonians v Old Eastbournians | Arundel Castle Cricket Club Ground, Arundel | 2017 |
| 4 | Old Wellingtonians v Old Millfieldians | Wellington College, Crowthorne | 2022 |
| 3 | Old Wellingtonians v Eton Ramblers | Wellington College, Crowthorne | 1985 |
| 3 | Old Wellingtonians v Charterhouse Friars | Charterhouse School, Godalming | 1986 |
| 3 | Old Wellingtonians v Eton Ramblers | Wellington College, Crowthorne | 1988 |
| 3 | Old Wellingtonians v Uppingham Rovers | Wellington College, Crowthorne | 1996 |
| 3 | Old Wellingtonians v Repton Pilgrims | Wellington College, Crowthorne | 1999 |
| 3 | Old Wellingtonians v Downside Wanderers | Wellington College, Crowthorne | 2001 |
| 3 | Old Wellingtonians v Eton Ramblers | Wellington College, Crowthorne | 2001 |
| 3 | Old Wellingtonians v Old Malvernians | Malvern College Ground, Malvern | 2005 |
| 3 | Old Wellingtonians v Radley Rangers | Wellington College, Crowthorne | 2006 |
| 3 | Old Wellingtonians v Stowe Templars | Stowe School Ground, Stowe | 2010 |
| 3 | Old Wellingtonians v Eton Ramblers | Upper Club, Eton College | 2015 |
| 3 | Old Wellingtonians v Charterhouse Friars | Wellington College, Crowthorne | 2017 |
| 3 | Old Wellingtonians v Rugby Meteors | Rugby School Ground, Rugby | 2018 |
| 3 | Old Wellingtonians v Old Cranleighans | Wellington College, Crowthorne | 2022 |
| 3 | Old Wellingtonians v Oundle Rovers | Oundle School Ground, Oundle | 2023 |
| 3 | Old Wellingtonians v Old Hamptonians | Hampton School, Hampton | 2024 |
