| 9 | Old Wykehamists v Haileybury Hermits | Haileybury College Ground, Hertford | 1969 |
| 8 | Old Wykehamists v Old Merchant Taylors | Durrants Sports Ground, Croxley Green | 1970 |
| 8 | Old Wykehamists v Charterhouse Friars | Charterhouse School, Godalming | 1982 |
| 8 | Old Wykehamists v Eton Ramblers | Upper Club, Eton College | 1985 |
| 8 | Old Wykehamists v Marlborough Blues | Ridding Field, Winchester | 1986 |
| 8 | Old Wykehamists v Old Wellingtonians | Ridding Field, Winchester | 2003 |
| 7 | Old Wykehamists v Old Malvernians | Malvern College Ground, Malvern | 1967 |
| 7 | Old Wykehamists v Repton Pilgrims | Repton School Ground, Repton | 1968 |
| 7 | Old Wykehamists v Old Tonbridgians | Ridding Field, Winchester | 1971 |
| 7 | Old Wykehamists v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 1972 |
| 7 | Old Wykehamists v Downside Wanderers | Downside School, Stratton-on-the-Fosse | 1981 |
| 7 | Old Wykehamists v Old Merchant Taylors | Ridding Field, Winchester | 1982 |
| 7 | Old Wykehamists v Old Cheltonians | Ridding Field, Winchester | 1985 |
| 7 | Old Wykehamists v Old Malvernians | Malvern College Ground, Malvern | 1990 |
| 7 | Old Wykehamists v Radley Rangers | Radley College Bigside Ground, Abingdon | 2009 |
| 7 | Old Wykehamists v Old Wellingtonians | Wellington College, Crowthorne | 2012 |
| 7 | Old Wykehamists v Charterhouse Friars | Ridding Field, Winchester | 2013 |
| 6 | Old Wykehamists v Old Cliftonians | Ridding Field, Winchester | 1970 |
| 6 | Old Wykehamists v Charterhouse Friars | Charterhouse School, Godalming | 1975 |
| 6 | Old Wykehamists v Oundle Rovers | Ridding Field, Winchester | 1981 |
| 6 | Old Wykehamists v Old Malvernians | Burton's Court, Chelsea | 1982 |
| 6 | Old Wykehamists v Bradfield Waifs | Bradfield College, Reading | 1985 |
| 6 | Old Wykehamists v Felsted Robins | Ridding Field, Winchester | 2002 |
| 6 | Old Wykehamists v Old Cliftonians | Clifton College Close Ground, Clifton | 2012 |
| 6 | Old Wykehamists v Old Eastbournians | Ridding Field, Winchester | 2017 |
| 5 | Old Wykehamists v Old Tonbridgians | Burton's Court, Chelsea | 1970 |
| 5 | Old Wykehamists v Repton Pilgrims | Ridding Field, Winchester | 1974 |
| 5 | Old Wykehamists v Old Cholmeleians | Highgate School Ground, Highgate | 1980 |
| 5 | Old Wykehamists v Old Cheltonians | Ridding Field, Winchester | 1993 |
| 5 | Old Wykehamists v Stowe Templars | Stowe School Ground, Stowe | 1994 |
| 5 | Old Wykehamists v Stowe Templars | Ridding Field, Winchester | 1996 |
| 5 | Old Wykehamists v Old Whitgiftians | Ridding Field, Winchester | 1998 |
| 5 | Old Wykehamists v Downside Wanderers | Ridding Field, Winchester | 2000 |
| 5 | Old Wykehamists v Stowe Templars | Ridding Field, Winchester | 2014 |
| 5 | Old Wykehamists v Old Cranleighans | Ridding Field, Winchester | 2016 |
| 5 | Old Wykehamists v Stowe Templars | Ridding Field, Winchester | 2021 |
