| 6 | Downside Wanderers v Old Wykehamists | Ridding Field, Winchester | 1969 |
| 5 | Downside Wanderers v Old Malvernians | Vincent Square, Westminster | 1986 |
| 5 | Downside Wanderers v Old Tonbridgians | Downside School, Stratton-on-the-Fosse | 1993 |
| 5 | Downside Wanderers v Stowe Templars | Stowe School Ground, Stowe | 2005 |
| 5 | Downside Wanderers v Haileybury Hermits | Haileybury College Ground, Hertford | 2008 |
| 4 | Downside Wanderers v Old Wellingtonians | Wellington College, Crowthorne | 1971 |
| 4 | Downside Wanderers v Radley Rangers | Downside School, Stratton-on-the-Fosse | 1975 |
| 4 | Downside Wanderers v Old Whitgiftians | Downside School, Stratton-on-the-Fosse | 1979 |
| 4 | Downside Wanderers v Haileybury Hermits | Haileybury College Ground, Hertford | 1991 |
| 4 | Downside Wanderers v Bradfield Waifs | Downside School, Stratton-on-the-Fosse | 1997 |
| 4 | Downside Wanderers v Repton Pilgrims | Downside School, Stratton-on-the-Fosse | 2006 |
| 4 | Downside Wanderers v Sherborne Pilgrims | Downside School, Stratton-on-the-Fosse | 2013 |
| 4 | Downside Wanderers v Repton Pilgrims | Repton School Ground, Repton | 2019 |
| 3 | Downside Wanderers v Old Westminsters | Downside School, Stratton-on-the-Fosse | 1970 |
| 3 | Downside Wanderers v Old Cliftonians | Clifton College Close Ground, Clifton | 1972 |
| 3 | Downside Wanderers v Old Malvernians | Downside School, Stratton-on-the-Fosse | 1974 |
| 3 | Downside Wanderers v Old Wykehamists | Ridding Field, Winchester | 1976 |
| 3 | Downside Wanderers v Old Amplefordians | Downside School, Stratton-on-the-Fosse | 1977 |
| 3 | Downside Wanderers v St Edward's Martyrs | St Edward's School Ground, Oxford | 1978 |
| 3 | Downside Wanderers v Old Cholmeleians | Highgate School Ground, Highgate | 1980 |
| 3 | Downside Wanderers v Old Wykehamists | Downside School, Stratton-on-the-Fosse | 1981 |
| 3 | Downside Wanderers v Rugby Meteors | Rugby School Ground, Rugby | 1984 |
| 3 | Downside Wanderers v Old Alleynians | Dulwich College Ground, Dulwich | 1985 |
| 3 | Downside Wanderers v Old Brightonians | Downside School, Stratton-on-the-Fosse | 1988 |
| 3 | Downside Wanderers v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 1990 |
| 3 | Downside Wanderers v Old Malvernians | Downside School, Stratton-on-the-Fosse | 1995 |
| 3 | Downside Wanderers v Old Alleynians | Downside School, Stratton-on-the-Fosse | 1996 |
| 3 | Downside Wanderers v Radley Rangers | Radley College Bigside Ground, Abingdon | 1999 |
| 3 | Downside Wanderers v Old Wykehamists | Ridding Field, Winchester | 2000 |
| 3 | Downside Wanderers v Old Westminsters | Vincent Square, Westminster | 2002 |
| 3 | Downside Wanderers v Old Malvernians | Downside School, Stratton-on-the-Fosse | 2007 |
| 3 | Downside Wanderers v Charterhouse Friars | Downside School, Stratton-on-the-Fosse | 2010 |
| 3 | Downside Wanderers v Oundle Rovers | Oundle School Ground, Oundle | 2012 |
| 3 | Downside Wanderers v Charterhouse Friars | Downside School, Stratton-on-the-Fosse | 2013 |
| 3 | Downside Wanderers v Marlborough Blues | Marlborough College Ground, Marlborough | 2025 |
