| Year | Winner | Club |
|---|---|---|
| 1955 | F Terry | Gatley Recreation |
| 1956 | J Smith | Cheadle Conservative |
| 1957 | A L Chandley | Cheadle Recreation |
| 1958 | J Lindley | Cheadle Recreation |
| 1959 | A Peters | Cheadle Recreation |
| 1960 | A Waters | Jolly Carter |
| 1961 | W Hearne | Cheadle Recreation |
| 1962 | J Marshall | Cross Keys |
| 1963 | J Morris | Didsbury Park |
| 1964 | C Yarwood | Simon Carves |
| 1965 | D Burch | Cheadle Conservative |
| 1966 | J Forrest | Thorn Grove |
| 1967 | E Leach | Greyhound |
| 1968 | J Morris | Fletcher Moss |
| 1969 | J Kelly | Cheadle Heath |
| 1970 | J B King | Farmers Arms |
| 1971 | J Kelly | Cheadle Heath |
| 1972 | J Kelly | Cheadle Heath |
| 1973 | E Smith | Fletcher Moss |
| 1974 | K Hardman | Gatley Recreation |
| 1975 | E Smith | Fletcher Moss |
| 1976 | J B King | Farmers Arms |
| 1977 | E Smith | Albert Club |
| 1978 | E W Brunyee | Gatley Recreation |
| 1979 | H Jolly | Heaton Mersey |
| 1980 | G Alsop | Heaton Mersey |
| 1981 | H Smith | Cheadle Conservative |
| 1982 | B Metcalfe | Cheadle Conservative |
| 1983 | N Garlick | Albert Club |
| 1984 | T Frahill | Heald Green Social Club |
| 1985 | P Knaggs | Cheadle Conservative |
| 1986 | S E Warburton | Gatley Recreation |
| 1987 | M Savage | Green End |
| 1988 | P Cosgrave | Waggon & Horses |
| 1989 | A Bradley | Green End |
| 1990 | S E Warburton | Gatley Recreation |
| 1991 | E Smith | Albert Club |
| 1992 | E Jebb | Green End |
| 1993 | A Jeavons | Withington |
| 1994 | K Kenyon | Stockport Cricket Club |
| 1995 | R Manuel | S Manchester British Legion |
| 1996 | B Turner | Green End |
| 1997 | K Kelly | Waggon & Horses |
| 1998 | K Walsh | Bungalow |
| 1999 | H Smith | Cheadle Conservative |
| 2000 | Dave Thompson | Heald Green Social Club |
| 2001 | Kevin Walsh | Bungalow |
| 2002 | Tony O'Donnell | Heald Green Social Club |
| 2003 | John Davies | Silverwings |
| 2004 | Dave Thompson | Heald Green Social Club |
| 2005 | E Ridgway | Cheadle Heath |
| 2008 | D Thompson | Heald Green |
| 2009 | Jon Mather | Shaw Heath |
| 2010 | David Thompson | Heald Green |
| 2011 | Kevin Wilson | Ladybridge Park |
| 2012 | John Spreadborough | Ladybridge Park |
| 2013 | John Clare | Northenden Social |
| 2014 | Ivor Hulme | Friendship |
| 2015 | Chris Barlow | Didsbury BC |
| 2016 | Hamilton | |
| 2017 | Savery | |
| 2018 | Dawson | |
| 2019 | Clare |