| 4 | Old Wykehamists v Stowe Templars | Stowe School Ground, Stowe | 1997 |
| 4 | Old Wykehamists v Bradfield Waifs | Ridding Field, Winchester | 2018 |
| 3 | Old Wykehamists v Downside Wanderers | Ridding Field, Winchester | 2001 |
| 2 | Old Wykehamists v Repton Pilgrims | Repton School Ground, Repton | 1968 |
| 2 | Old Wykehamists v Charterhouse Friars | Charterhouse School, Godalming | 1975 |
| 2 | Old Wykehamists v Oundle Rovers | Oundle School Ground, Oundle | 1979 |
| 2 | Old Wykehamists v Old Cholmeleians | Highgate School Ground, Highgate | 1980 |
| 2 | Old Wykehamists v Old Malvernians | Ridding Field, Winchester | 1983 |
| 2 | Old Wykehamists v Oundle Rovers | Ridding Field, Winchester | 1995 |
| 2 | Old Wykehamists v Radley Rangers | Radley College Bigside Ground, Abingdon | 1999 |
| 2 | Old Wykehamists v Downside Wanderers | Ridding Field, Winchester | 2000 |
| 2 | Old Wykehamists v Haileybury Hermits | Ridding Field, Winchester | 2004 |
| 2 | Old Wykehamists v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 2007 |
| 2 | Old Wykehamists v Felsted Robins | Felsted School Ground, Dunmow | 2011 |
| 2 | Old Wykehamists v Old Wellingtonians | Wellington College, Crowthorne | 2014 |
| 2 | Old Wykehamists v Uppingham Rovers | Upper Field, Uppingham School | 2016 |
| 2 | Old Wykehamists v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 2017 |
| 2 | Old Wykehamists v Old Merchant Taylors | Merchant Taylors' School Ground, Northwood | 2019 |
| 2 | Old Wykehamists v Rugby Meteors | Ridding Field, Winchester | 2022 |
| 1 | Old Wykehamists v Old Malvernians | Malvern College Ground, Malvern | 1967 |
| 1 | Old Wykehamists v Old Cliftonians | Ridding Field, Winchester | 1970 |
| 1 | Old Wykehamists v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 1973 |
| 1 | Old Wykehamists v Downside Wanderers | Downside School, Stratton-on-the-Fosse | 1981 |
| 1 | Old Wykehamists v Bradfield Waifs | Bradfield College, Reading | 1981 |
| 1 | Old Wykehamists v Old Malvernians | Burton's Court, Chelsea | 1982 |
| 1 | Old Wykehamists v Old Malvernians | Ridding Field, Winchester | 1984 |
| 1 | Old Wykehamists v Old Cheltonians | Ridding Field, Winchester | 1985 |
| 1 | Old Wykehamists v Bradfield Waifs | Bradfield College, Reading | 1985 |
| 1 | Old Wykehamists v Oundle Rovers | Oundle School Ground, Oundle | 1985 |
| 1 | Old Wykehamists v Repton Pilgrims | Repton School Ground, Repton | 1986 |
| 1 | Old Wykehamists v Oundle Rovers | Oundle School Ground, Oundle | 1987 |
| 1 | Old Wykehamists v Radley Rangers | Radley College Bigside Ground, Abingdon | 1987 |
| 1 | Old Wykehamists v Old Cheltonians | Ridding Field, Winchester | 1993 |
| 1 | Old Wykehamists v Stowe Templars | Stowe School Ground, Stowe | 1994 |
| 1 | Old Wykehamists v Stowe Templars | Ridding Field, Winchester | 1996 |
| 1 | Old Wykehamists v Old Whitgiftians | Ridding Field, Winchester | 1998 |
| 1 | Old Wykehamists v Felsted Robins | Ridding Field, Winchester | 2002 |
| 1 | Old Wykehamists v Old Wellingtonians | Ridding Field, Winchester | 2003 |
| 1 | Old Wykehamists v Charterhouse Friars | Ridding Field, Winchester | 2005 |
| 1 | Old Wykehamists v Old Cliftonians | Ridding Field, Winchester | 2008 |
| 1 | Old Wykehamists v Radley Rangers | Radley College Bigside Ground, Abingdon | 2009 |
| 1 | Old Wykehamists v Old Cliftonians | Clifton College Close Ground, Clifton | 2012 |
| 1 | Old Wykehamists v Harrow Wanderers | Ridding Field, Winchester | 2012 |
| 1 | Old Wykehamists v Charterhouse Friars | Ridding Field, Winchester | 2013 |
| 1 | Old Wykehamists v Rugby Meteors | Ridding Field, Winchester | 2014 |
| 1 | Old Wykehamists v Old Alleynians | Dulwich College Ground, Dulwich | 2015 |
| 1 | Old Wykehamists v Oundle Rovers | Ridding Field, Winchester | 2015 |
| 1 | Old Wykehamists v Old Whitgiftians | Ridding Field, Winchester | 2016 |
| 1 | Old Wykehamists v Stowe Templars | Ridding Field, Winchester | 2021 |
