| 7 | Old Whitgiftians v Lancing Rovers | Croham Manor Road, Croydon | 1982 |
| 6 | Old Whitgiftians v Old Cliftonians | Clifton College Close Ground, Clifton | 2000 |
| 5 | Old Whitgiftians v Old Westminsters | Vincent Square, Westminster | 1976 |
| 5 | Old Whitgiftians v Charterhouse Friars | Whitgift School, Croydon | 1993 |
| 5 | Old Whitgiftians v Stowe Templars | Stowe School Ground, Stowe | 2001 |
| 5 | Old Whitgiftians v Marlborough Blues | Marlborough College Ground, Marlborough | 2005 |
| 5 | Old Whitgiftians v Haileybury Hermits | Haileybury College Ground, Hertford | 2007 |
| 4 | Old Whitgiftians v Old Blundellians | Blundell's School, Tiverton | 1977 |
| 4 | Old Whitgiftians v Rugby Meteors | Whitgift School, Croydon | 1980 |
| 4 | Old Whitgiftians v Charterhouse Friars | Whitgift School, Croydon | 1991 |
| 4 | Old Whitgiftians v Old Merchant Taylors | Whitgift School, Croydon | 1998 |
| 3 | Old Whitgiftians v Uppingham Rovers | Upper Field, Uppingham School | 1969 |
| 3 | Old Whitgiftians v Downside Wanderers | Downside School, Stratton-on-the-Fosse | 1979 |
| 3 | Old Whitgiftians v Eton Ramblers | Croham Manor Road, Croydon | 1985 |
| 3 | Old Whitgiftians v Old Westminsters | Whitgift School, Croydon | 1993 |
| 3 | Old Whitgiftians v Felsted Robins | Whitgift School, Croydon | 1996 |
| 3 | Old Whitgiftians v Rugby Meteors | Rugby School Ground, Rugby | 1997 |
| 3 | Old Whitgiftians v Old Wykehamists | Ridding Field, Winchester | 1998 |
| 3 | Old Whitgiftians v Charterhouse Friars | Charterhouse School, Godalming | 2002 |
| 3 | Old Whitgiftians v Uppingham Rovers | Middle Field Pitch 1, Uppingham School | 2006 |
| 3 | Old Whitgiftians v Old Wykehamists | Ridding Field, Winchester | 2016 |
| 2 | Old Whitgiftians v Charterhouse Friars | Whitgift School, Croydon | 1972 |
| 2 | Old Whitgiftians v Felsted Robins | Whitgift School, Croydon | 1978 |
| 2 | Old Whitgiftians v Radley Rangers | Radley College Bigside Ground, Abingdon | 1981 |
| 2 | Old Whitgiftians v Haileybury Hermits | Haileybury College Ground, Hertford | 1984 |
| 2 | Old Whitgiftians v Marlborough Blues | Marlborough College Ground, Marlborough | 1986 |
| 2 | Old Whitgiftians v Uppingham Rovers | Middle Field Pitch 1, Uppingham School | 1987 |
| 2 | Old Whitgiftians v Marlborough Blues | Marlborough College Ground, Marlborough | 1995 |
| 2 | Old Whitgiftians v Bradfield Waifs | Bradfield College, Reading | 2000 |
| 2 | Old Whitgiftians v Old Cholmeleians | Whitgift School, Croydon | 2008 |
| 2 | Old Whitgiftians v Eton Ramblers | Whitgift School, Croydon | 2009 |
| 2 | Old Whitgiftians v Radley Rangers | Whitgift School, Croydon | 2014 |
| 2 | Old Whitgiftians v Downside Wanderers | Downside School, Stratton-on-the-Fosse | 2015 |
| 2 | Old Whitgiftians v Old Wellingtonians | Wellington College, Crowthorne | 2015 |
