Renamed from the 'Sussex Express Singles' in season 2018/19
| Year | Winner | Team | Runner Up | Team | |
|---|---|---|---|---|---|
| 2024/25 | H Jackson | Dorset B | C Thomas | Dorset B | |
| 2023/24 | H Jackson | Dorset A | C Thomas | Dorset B | |
| 2022/23 | M Jordan | St Marys | H Jackson | Dorset | |
| 2021/22 | A Davis | Brewers | J Hubbard | Tally Ho B | |
| 2020/21 | - | - | - | - | |
| 2019/20 | - | - | - | - | |
| 2018/19 | H Jackson | Dorset A | F Jackson | Dorset A | |
| 2017/18 | R Rodford | Tally Ho B | S Geer | St Marys | |
| 2016/17 | M Whiting | Con Club | P Dickens | Green Man | |
| 2015/16 | M Jordan | Con Club | D N Sains | Tally Ho B | |
| 2014/15 | M Whiting | Con Club | S Jackson | Tally Ho Wanderers | |
| 2013/14 | D Harding | Tally Ho B | M Jordan | Tally Ho Wanderers | |
| 2012/13 | R Harding jnr | Tally Ho B | G Day | St Marys | |
| 2011/12 | M Whiting | Con Club | R Blay | Brewers | |
| 2010/11 | R Blay | Brewers | M Whiting | Con Club | |
| 2009/10 | R Blay | Brewers | R Harding jnr | Tally Ho B | |
| 2008/09 | R Blay | Bridgeview | S Bastone | Pelham A | |
| 2007/08 | R Blay | Bridgeview | M Jordan | Pelham A | |
| 2006/07 | M Whiting | Pelham A | D N Sains | Tally Ho B | |
| 2005/06 | R Blay | Bridgeview | R Harding jnr | Tally Ho B | |
| 2004/05 | A Davis | Bridgeview | D N Sains | Tally Ho X | |
| 2003/04 | R Blay | Bridgeview | |||
| 2002/03 | R Blay | Bridgeview | M Whiting | Volunteer A | |
| 2001/02 | M Whiting | Volunteer A | P Dickens | Glynde WMC | |
| 2000/01 | D N Sains | Volunteer A | D Harding | Volunteer A | |
| 1999/00 | R Harding | Tally Ho B | S Bastone | Meridian A | |
| 1998/99 | R Harding | Pelham A | |||
| 1997/98 | A Gay | Lamb A | |||
| 1996/97 | R Hammond | Trevor Arms | |||
| 1995/96 | R Hammond | Trevor Arms | |||
| 1994/95 | R Goldsmith | Black Horse | |||
| 1993/94 | P Tomsett | Malling | |||
| 1992/93 | not recorded | not recorded | |||
| 1991/92 | R Howick | Green Man | |||
| 1990/91 | not recorded | not recorded | |||
| 1989/90 | I Smart | Malling A | |||
| 1988/89 | not recorded | not recorded | |||
| 1987/88 | A Jordan | St Marys C | |||
| 1986/87 | R Harding | Portland | |||
| 1985/86 | G Whiting | St Michaels CC | |||
| 1984/85 | G Whiting | St Michaels CC | |||
| 1983/84 | P Telford | St Michaels CC | |||
| 1982/83 | R Harding | Tally Ho | |||
| 1981/82 | R Harding | Tally Ho | |||
| 1980/81 | G Lewis | Royal Oak | |||
| 1979/80 | S Arkwell | Tally Ho | |||
| 1978/79 | M Moody | Fruiterers | |||
| 1977/78 | D Weller | Jolly Friars | |||
| 1976/77 | D Smith | Fruiterers | |||
| 1975/76 | D Hill | Jolly Friars | |||
| 1974/75 | R Harris | Jolly Friars | |||
| 1973/74 | T Steggall | British Legion | |||
| 1972/73 | E Willard | Dorset Arms | |||
| 1971/72 | D Ottley | Jolly Friars | |||
| 1970/71 | D Smith | Tally Ho | |||
| 1969/70 | D Smith | Legion | |||
| 1968/69 | J Lennard | Rainbow | |||
| 1967/68 | W Milham | Royal Oak | |||
| 1966/67 | D Ottley | Jolly Friars | |||
| 1965/66 | J Cole | Royal Oak | |||
| 1964/65 | D Smith | Royal Oak | |||
| 1963/64 | D Ottley | Jolly Friars | |||
| 1962/63 | D Smith | Bell Inn | |||
| 1961/62 | J Cole | Royal Oak | |||
| 1960/61 | J Cole | Royal Oak | |||
| 1959/60 | D Ottley | Jolly Friars | |||
| 1958/59 | D Ottley | Jolly Friars | |||
| 1957/58 | J Carter | Jolly Friars | |||
| 1956/57 | D Smith | Fruiterers | |||
| 1955/56 | D Ottley | Phoenix Sports | |||
| 1954/55 | L Brown | Gardeners Arms |