| 02 Jun 1996 | The Cricketer Cup 1996 | First Round | Downside Wanderers v Old Alleynians |
| 15 Jun 2003 | The Cricketer Cup 2003 | First Round | Downside Wanderers v Old Amplefordians |
| 13 Jun 2004 | The Cricketer Cup 2004 | First Round | Downside Wanderers v Old Amplefordians |
| 11 Jun 2006 | The Cricketer Cup 2006 | First Round | Downside Wanderers v Repton Pilgrims |
| 10 Jun 2007 | The Cricketer Cup 2007 | First Round | Downside Wanderers v Old Malvernians |
| 15 Jun 2008 | The Cricketer Cup 2008 | First Round | Downside Wanderers v Shrewsbury Saracens |
| 31 May 1970 | The Cricketer Cup 1970 | First Round | Downside Wanderers v Old Westminsters |
| 30 May 1971 | The Cricketer Cup 1971 | First Round | Downside Wanderers v Old Wellingtonians |
| 31 May 1992 | The Cricketer Cup 1992 | First Round | Downside Wanderers v Sherborne Pilgrims |
| 02 Jun 1974 | The Cricketer Cup 1974 | First Round | Downside Wanderers v Old Malvernians |
| 01 Jun 1975 | The Cricketer Cup 1975 | First Round | Downside Wanderers v Radley Rangers |
| 19 Jun 1977 | The Cricketer Cup 1977 | Second Round | Downside Wanderers v Old Amplefordians |
| 03 Jun 1979 | The Cricketer Cup 1979 | First Round | Downside Wanderers v Rugby Meteors |
| 17 Jun 1979 | The Cricketer Cup 1979 | Second Round | Downside Wanderers v Old Whitgiftians |
| 31 May 1981 | The Cricketer Cup 1981 | First Round | Downside Wanderers v Old Wykehamists |
| 30 May 1982 | The Cricketer Cup 1982 | First Round | Downside Wanderers v Old Westminsters |
| 13 Jun 1982 | The Cricketer Cup 1982 | Second Round | Downside Wanderers v Old Whitgiftians |
| 03 Jun 1984 | The Cricketer Cup 1984 | First Round | Downside Wanderers v Radley Rangers |
| 17 Jun 1984 | The Cricketer Cup 1984 | Second Round | Downside Wanderers v Marlborough Blues |
| 31 May 1987 | The Cricketer Cup 1987 | First Round | Downside Wanderers v Haileybury Hermits |
| 19 Jun 1988 | The Cricketer Cup 1988 | Second Round | Downside Wanderers v Old Brightonians |
| 25 Jun 1989 | The Cricketer Cup 1989 | Second Round | Downside Wanderers v Old Tonbridgians |
| 03 Jun 1990 | The Cricketer Cup 1990 | First Round | Downside Wanderers v Old Amplefordians |
| 30 May 1993 | The Cricketer Cup 1993 | First Round | Downside Wanderers v Old Tonbridgians |
| 19 Jun 1994 | The Cricketer Cup 1994 | Second Round | Downside Wanderers v Bradfield Waifs |
| 18 Jun 1995 | The Cricketer Cup 1995 | First Round | Downside Wanderers v Old Westminsters |
| 25 Jun 1995 | The Cricketer Cup 1995 | Second Round | Downside Wanderers v Charterhouse Friars |
| 09 Jul 1995 | The Cricketer Cup 1995 | Quarter-Final | Downside Wanderers v Old Brightonians |
| 23 Jul 1995 | The Cricketer Cup 1995 | Semi-Final | Downside Wanderers v Old Malvernians |
| 01 Jun 1997 | The Cricketer Cup 1997 | First Round | Downside Wanderers v Bradfield Waifs |
| 13 Jun 2010 | The Cricketer Cup 2010 | First Round | Downside Wanderers v Haileybury Hermits |
| 04 Jul 2010 | The Cricketer Cup 2010 | Second Round | Downside Wanderers v Charterhouse Friars |
| 16 Jun 2013 | The Cricketer Cup 2013 | First Round | Downside Wanderers v Sherborne Pilgrims |
| 30 Jun 2013 | The Cricketer Cup 2013 | Second Round | Downside Wanderers v Charterhouse Friars |
| 15 Jun 2014 | The Cricketer Cup 2014 | First Round | Downside Wanderers v Oundle Rovers |
| 14 Jun 2015 | The Cricketer Cup 2015 | First Round | Downside Wanderers v Old Whitgiftians |
| 17 Jun 2012 | The Cricketer Cup 2012 | First Round | Downside Wanderers v Oundle Rovers |
| 13 Jun 2021 | The Cricketer Cup 2021 | First Round | Downside Wanderers v Old Cheltonians |
| 12 Jun 2022 | The Cricketer Cup 2022 | First Round | Downside Wanderers v Old Cranleighans |
| 09 Jun 2024 | The Cricketer Cup 2024 | First Round | Downside Wanderers v Harrow Wanderers |
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