| 15 Jun 1969 | The Cricketer Cup 1969 | Second Round | Old Brightonians v Felsted Robins |
| 06 Jul 1969 | The Cricketer Cup 1969 | Quarter-Final | Old Brightonians v Rugby Meteors |
| 27 Jul 1969 | The Cricketer Cup 1969 | Semi-Final | Old Brightonians v Old Malvernians |
| 23 Jun 1996 | The Cricketer Cup 1996 | Second Round | Old Brightonians v Repton Pilgrims |
| 02 Jun 2002 | The Cricketer Cup 2002 | First Round | Old Brightonians v Radley Rangers |
| 30 Jun 2002 | The Cricketer Cup 2002 | Quarter-Final | Old Brightonians v Shrewsbury Saracens |
| 15 Jun 2003 | The Cricketer Cup 2003 | First Round | Old Brightonians v Sherborne Pilgrims |
| 25 Jul 2004 | The Cricketer Cup 2004 | Semi-Final | Old Brightonians v Old Malvernians |
| 12 Jun 2005 | The Cricketer Cup 2005 | First Round | Old Brightonians v Old Amplefordians |
| 11 Jun 2006 | The Cricketer Cup 2006 | First Round | Old Brightonians v Harrow Wanderers |
| 10 Jun 2007 | The Cricketer Cup 2007 | First Round | Old Brightonians v Oundle Rovers |
| 15 Jun 2008 | The Cricketer Cup 2008 | First Round | Old Brightonians v Rugby Meteors |
| 14 Jun 2009 | The Cricketer Cup 2009 | First Round | Old Brightonians v Uppingham Rovers |
| 31 May 1970 | The Cricketer Cup 1970 | First Round | Old Brightonians v Old Amplefordians |
| 28 May 1972 | The Cricketer Cup 1972 | First Round | Old Brightonians v Old Amplefordians |
| 17 Jun 1973 | The Cricketer Cup 1973 | Second Round | Old Brightonians v Charterhouse Friars |
| 16 Jun 1974 | The Cricketer Cup 1974 | Second Round | Old Brightonians v Old Malvernians |
| 05 Jun 1977 | The Cricketer Cup 1977 | First Round | Old Brightonians v Downside Wanderers |
| 04 Jun 1978 | The Cricketer Cup 1978 | First Round | Old Brightonians v Uppingham Rovers |
| 17 Jun 1979 | The Cricketer Cup 1979 | Second Round | Old Brightonians v Radley Rangers |
| 08 Jul 1979 | The Cricketer Cup 1979 | Quarter-Final | Old Brightonians v Downside Wanderers |
| 05 Aug 1979 | The Cricketer Cup 1979 | Semi-Final | Old Brightonians v Uppingham Rovers |
| 01 Jun 1980 | The Cricketer Cup 1980 | First Round | Old Brightonians v Old Blundellians |
| 22 May 1983 | The Cricketer Cup 1983 | First Round | Old Brightonians v Radley Rangers |
| 01 Jun 1986 | The Cricketer Cup 1986 | First Round | Old Brightonians v Haileybury Hermits |
| 29 May 1988 | The Cricketer Cup 1988 | First Round | Old Brightonians v Uppingham Rovers |
| 02 Jun 1991 | The Cricketer Cup 1991 | First Round | Old Brightonians v Old Malvernians |
| 30 Jun 1991 | The Cricketer Cup 1991 | Second Round | Old Brightonians v Old Cliftonians |
| 31 May 1992 | The Cricketer Cup 1992 | First Round | Old Brightonians v Rugby Meteors |
| 21 Jun 1992 | The Cricketer Cup 1992 | Second Round | Old Brightonians v Eton Ramblers |
| 30 May 1993 | The Cricketer Cup 1993 | First Round | Old Brightonians v Old Cholmeleians |
| 20 Jun 1993 | The Cricketer Cup 1993 | Second Round | Old Brightonians v Old Cliftonians |
| 04 Jun 1995 | The Cricketer Cup 1995 | First Round | Old Brightonians v Old Blundellians |
| 25 Jun 1995 | The Cricketer Cup 1995 | Second Round | Old Brightonians v Oundle Rovers |
| 01 Jun 1997 | The Cricketer Cup 1997 | First Round | Old Brightonians v Oundle Rovers |
| 21 Jun 1998 | The Cricketer Cup 1998 | Second Round | Old Brightonians v Old Tonbridgians |
| 30 May 1999 | The Cricketer Cup 1999 | First Round | Old Brightonians v Old Cheltonians |
| 04 Jul 2010 | The Cricketer Cup 2010 | Second Round | Old Brightonians v Old Tonbridgians |
| 18 Jul 2010 | The Cricketer Cup 2010 | Quarter-Final | Old Brightonians v Charterhouse Friars |
| 10 Jun 2001 | The Cricketer Cup 2001 | First Round | Old Brightonians v Haileybury Hermits |
| 24 Jun 2001 | The Cricketer Cup 2001 | Second Round | Old Brightonians v Old Westminsters |
| 08 Jul 2001 | The Cricketer Cup 2001 | Quarter-Final | Old Brightonians v Eton Ramblers |
| 17 Jun 2012 | The Cricketer Cup 2012 | First Round | Old Brightonians v Old Tonbridgians |
| 16 Jun 2013 | The Cricketer Cup 2013 | First Round | Old Brightonians v Harrow Wanderers |
| 12 Jun 2016 | The Cricketer Cup 2016 | First Round | Old Brightonians v Charterhouse Friars |
| 11 Jun 2017 | The Cricketer Cup 2017 | First Round | Old Brightonians v Old Wykehamists |
| 12 Jun 2022 | The Cricketer Cup 2022 | First Round | Old Brightonians v Old Merchant Taylors |
| 09 Jun 2024 | The Cricketer Cup 2024 | First Round | Old Brightonians v Old Cholmeleians |
| 30 Jun 2024 | The Cricketer Cup 2024 | Second Round | Old Brightonians v Charterhouse Friars |
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