| 5 | Old Wykehamists v Oundle Rovers | Oundle School Ground, Oundle | 1985 |
| 4 | Old Wykehamists v Stowe Templars | Stowe School Ground, Stowe | 1997 |
| 3 | Old Wykehamists v Repton Pilgrims | Repton School Ground, Repton | 1968 |
| 3 | Old Wykehamists v Haileybury Hermits | Haileybury College Ground, Hertford | 1969 |
| 3 | Old Wykehamists v Old Merchant Taylors | Durrants Sports Ground, Croxley Green | 1970 |
| 3 | Old Wykehamists v Oundle Rovers | Oundle School Ground, Oundle | 1979 |
| 3 | Old Wykehamists v Downside Wanderers | Downside School, Stratton-on-the-Fosse | 1981 |
| 3 | Old Wykehamists v Repton Pilgrims | Repton School Ground, Repton | 1986 |
| 3 | Old Wykehamists v Marlborough Blues | Ridding Field, Winchester | 1986 |
| 3 | Old Wykehamists v Marlborough Blues | Ridding Field, Winchester | 1992 |
| 3 | Old Wykehamists v Old Whitgiftians | Ridding Field, Winchester | 1998 |
| 3 | Old Wykehamists v Radley Rangers | Radley College Bigside Ground, Abingdon | 1999 |
| 3 | Old Wykehamists v Downside Wanderers | Ridding Field, Winchester | 2001 |
| 3 | Old Wykehamists v Felsted Robins | Felsted School Ground, Dunmow | 2011 |
| 3 | Old Wykehamists v Rugby Meteors | Ridding Field, Winchester | 2014 |
| 2 | Old Wykehamists v Old Tonbridgians | Burton's Court, Chelsea | 1970 |
| 2 | Old Wykehamists v Old Tonbridgians | Tonbridge School Ground, Tonbridge | 1972 |
| 2 | Old Wykehamists v Charterhouse Friars | Burton's Court, Chelsea | 1981 |
| 2 | Old Wykehamists v Charterhouse Friars | Charterhouse School, Godalming | 1982 |
| 2 | Old Wykehamists v Eton Ramblers | Upper Club, Eton College | 1985 |
| 2 | Old Wykehamists v Old Wellingtonians | Ridding Field, Winchester | 2003 |
| 2 | Old Wykehamists v Haileybury Hermits | Ridding Field, Winchester | 2004 |
| 2 | Old Wykehamists v Charterhouse Friars | Ridding Field, Winchester | 2005 |
| 2 | Old Wykehamists v Old Cliftonians | Ridding Field, Winchester | 2008 |
| 2 | Old Wykehamists v Radley Rangers | Radley College Bigside Ground, Abingdon | 2009 |
| 2 | Old Wykehamists v Radley Rangers | Ridding Field, Winchester | 2012 |
| 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 |
