| 5 | Downside Wanderers v Charterhouse Friars | Charterhouse School, Godalming | 2016 |
| 4 | Downside Wanderers v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 1982 |
| 4 | Downside Wanderers v Oundle Rovers | Downside School, Stratton-on-the-Fosse | 2014 |
| 3 | Downside Wanderers v Harrow Wanderers | Harrow School Cricket Ground, Harrow-on-the-Hill | 1990 |
| 3 | Downside Wanderers v Haileybury Hermits | Haileybury College Ground, Hertford | 1991 |
| 3 | Downside Wanderers v Old Malvernians | Downside School, Stratton-on-the-Fosse | 1995 |
| 3 | Downside Wanderers v Old Amplefordians | Downside School, Stratton-on-the-Fosse | 2004 |
| 3 | Downside Wanderers v Charterhouse Friars | Downside School, Stratton-on-the-Fosse | 2010 |
| 3 | Downside Wanderers v Old Whitgiftians | Downside School, Stratton-on-the-Fosse | 2015 |
| 2 | Downside Wanderers v Bradfield Waifs | Bradfield College, Reading | 1973 |
| 2 | Downside Wanderers v Old Wykehamists | Ridding Field, Winchester | 1976 |
| 2 | Downside Wanderers v Old Wykehamists | Downside School, Stratton-on-the-Fosse | 1981 |
| 2 | Downside Wanderers v Bradfield Waifs | Downside School, Stratton-on-the-Fosse | 1994 |
| 2 | Downside Wanderers v Bradfield Waifs | Downside School, Stratton-on-the-Fosse | 1997 |
| 2 | Downside Wanderers v Sherborne Pilgrims | Sherborne School, Sherborne | 2002 |
| 2 | Downside Wanderers v Stowe Templars | Stowe School Ground, Stowe | 2005 |
| 2 | Downside Wanderers v Charterhouse Friars | Downside School, Stratton-on-the-Fosse | 2013 |
| 2 | Downside Wanderers v St Edward's Martyrs | St Edward's School Ground, Oxford | 2018 |
| 2 | Downside Wanderers v Old Cranleighans | Downside School, Stratton-on-the-Fosse | 2022 |
| 2 | Downside Wanderers v Harrow Wanderers | Downside School, Stratton-on-the-Fosse | 2024 |
| 1 | Downside Wanderers v Old Amplefordians | Downside School, Stratton-on-the-Fosse | 1977 |
| 1 | Downside Wanderers v Rugby Meteors | Downside School, Stratton-on-the-Fosse | 1979 |
| 1 | Downside Wanderers v Old Whitgiftians | Downside School, Stratton-on-the-Fosse | 1979 |
| 1 | Downside Wanderers v Old Cholmeleians | Highgate School Ground, Highgate | 1980 |
| 1 | Downside Wanderers v Old Westminsters | Downside School, Stratton-on-the-Fosse | 1982 |
| 1 | Downside Wanderers v Rugby Meteors | Rugby School Ground, Rugby | 1984 |
| 1 | Downside Wanderers v Old Malvernians | Malvern College Ground, Malvern | 1984 |
| 1 | Downside Wanderers v Sherborne Pilgrims | Sherborne School, Sherborne | 1986 |
| 1 | Downside Wanderers v Lancing Rovers | Lancing College Ground, Lancing | 1986 |
| 1 | Downside Wanderers v Old Whitgiftians | Whitgift School, Croydon | 1988 |
| 1 | Downside Wanderers v Old Tonbridgians | Downside School, Stratton-on-the-Fosse | 1989 |
| 1 | Downside Wanderers v Old Amplefordians | Downside School, Stratton-on-the-Fosse | 1990 |
| 1 | Downside Wanderers v Old Tonbridgians | Downside School, Stratton-on-the-Fosse | 1993 |
| 1 | Downside Wanderers v Charterhouse Friars | Downside School, Stratton-on-the-Fosse | 1995 |
| 1 | Downside Wanderers v Old Brightonians | Downside School, Stratton-on-the-Fosse | 1995 |
| 1 | Downside Wanderers v Bradfield Waifs | Bradfield College, Reading | 1998 |
| 1 | Downside Wanderers v Old Wykehamists | Ridding Field, Winchester | 2000 |
| 1 | Downside Wanderers v Old Amplefordians | Downside School, Stratton-on-the-Fosse | 2003 |
| 1 | Downside Wanderers v Repton Pilgrims | Downside School, Stratton-on-the-Fosse | 2006 |
| 1 | Downside Wanderers v Shrewsbury Saracens | Downside School, Stratton-on-the-Fosse | 2008 |
| 1 | Downside Wanderers v Haileybury Hermits | Haileybury College Ground, Hertford | 2008 |
| 1 | Downside Wanderers v Haileybury Hermits | Downside School, Stratton-on-the-Fosse | 2010 |
| 1 | Downside Wanderers v Oundle Rovers | Oundle School Ground, Oundle | 2012 |
| 1 | Downside Wanderers v Sherborne Pilgrims | Downside School, Stratton-on-the-Fosse | 2013 |
| 1 | Downside Wanderers v Old Cholmeleians | Tivoli Road, Hornsey | 2016 |
| 1 | Downside Wanderers v Old Bedfordians | Whitehorn Lane, Letchworth | 2017 |
| 1 | Downside Wanderers v Repton Pilgrims | Repton School Ground, Repton | 2019 |
| 1 | Downside Wanderers v Old Cheltonians | Downside School, Stratton-on-the-Fosse | 2021 |
| 1 | Downside Wanderers v Marlborough Blues | Marlborough College Ground, Marlborough | 2025 |
