Award of Merit
| Year | Winner | Club |
| 2009 | G Davies | Wharton Cons |
| 2008 | J Cornes | Castle Private |
| C Macdonald | Castle Private | |
| 2007 | C Bebbington | Lloyds Hotel |
| 2006 | S Ridley | Lloyds Hotel |
| 2005 | M Geraghty | Lloyds Hotel |
| 2004 | E German | Budenburgs |
| 2003 | I Broadhurst | Nursery |
| 2002 | R Crawshaw | Wilmslow |
| S Ridley | Lloyds Hotel | |
| G Telford | Budenburgs | |
| 2001 | M Geraghty | Lloyds BC |
| 2000 | G Telford | Sale |
| Year | Winner | Club |
| 1999 | C Morrison | Sale |
| G Telford | Sale | |
| 1998 | M Chamberlain | |
| 1997 | G Cookson | Wharton Cons |
| N Jenkinson | Nursery BC | |
| A Murray | Sale Excelsior | |
| 1996 | M Winnington | Owley Wood |
| 1995 | C McDonald | Wilmslow RBL |
| 1994 | G Cookson | Wharton Cons |
| 1993 | W Burlington | King & Queen |
| 1992 | F S Frith | Owley Wood |
| 1991 | F S Frith | Owley Wood |
| 1990 | P Paton | King & Queen |
| Year | Winner | Club |
| 1989 | J Gurney | Stonemasons Arms |
| 1988 | P Scott | Owley Wood |
| 1985 | R Crawshaw | Wilmslow RBL |
| 1984 | K Whitelow | Cherry Grove |
| 1983 | B Cookson | Wharton Cons |
| G Cookson | Wharton Cons | |
| 1982 | F S Frith | Farmers Arms (Rudheath) |
| A Murray | Linotype | |
| 1981 | G Donnelly | Winsford Liberal Club |
| G Vernon | Winsford Liberal Club | |
| 1980 | K Birkett | Farmers Arms (Rudheath) |
| F S Frith | Farmers Arms (Rudheath) | |
| Year | Winner | Club |
| 1979 | F Gartside | Houldsworth WMC |
| 1978 | K Birkett | Farmers Arms (Rudheath) |
| 1977 | F Gartside | Houldsworth WMC |
| T Heyes jnr | Stalybridge Rec | |
| 1976 | D Mercer | Houldsworth WMC |
| B Cookson | Wharton Rec | |
| 1975 | D Mercer | Houldsworth WMC |
| 1974 | D Mercer | Houldsworth WMC |
| 1973 | J Hunt | Winsford Liberal Club |
| 1972 | J Hunt | Winsford Liberal Club |
| 1971 | D Mercer | Houldsworth WMC |
| 1970 | N Metcalfe | Union Club |
| W H Smith | Kings BC | |
| Glyn Vernon | Winsford Liberal Club | |
| Year | Winner | Club |
| 1969 | F S Frith | Farmers Arms (Rudheath) |
| 1968 | K M Winnington | Winnington Pk Rec |
| E Winterbottom | George & Dragon (Hyde) | |
| 1967 | R Johnson | Winsford Liberal Club |
| 1966 | E Winterbottom | George & Dragon (Hyde) |
| 1965 | J Goulding | Farmers Arms (Rudheath) |
| 1964 | C A West | Sale Excelsior |
| K M Winnington | Winnington Pk Rec | |
| 1963 | F S Frith | Farmers Arms (Rudheath) |
| 1962 | C A West | Sale Excelsior |
| 1961 | R Cross | Union Club (Alderley Edge) |
| 1960 | No award | |
| Year | Winner | Club |
| 1959 | A Lewis | Farmers Arms (Rudheath) |
| 1958 | E Winterbottom | George & Dragon (Hyde) |
| 1957 | E Kelly | Grapes Hotel (Hyde) |
| 1956 | J Davies | Winsford Liberal Club |
| 1955 | E Lee | Stalybridge & Dukinfield Rec |
Junior Player of the Year
| Year | Winner | Club | |
| 2009 | S Smith | Offerton | |
| 2008 | D Moores | Comberbach | |
| 2007 | T Palin | Slow & Easy | |
| 2006 | T Vickers | Wharton Cons | |
| 2005 | D Moores | Comberbach | |
| 2004 | No player appointed | ||
| 2003 | No player appointed | ||
| 2002 | M Thurlwell | Comberbach | |
| 2001 | R Winnington | Hartford | |
| 2000 | S Cookson | Winsford | |
| Year | Winner | Club | |
| 1999 | L Fletcher | Stockport | |
| 1998 | A Morrison | ||
| R Winnington | Hartford | ||
| S Morrey (special award) | |||
| 1997 | Darren Burgess | Woodley Sports | |
| David Hamlett | Wharton Rec | ||
| Stuart Kellett | Comberbach | ||
| Steven Needham | Vernon Park | ||
| 1996 | Stuart Kellett | Comberbach | |
| Peter Morrison | Sale Excelsior | ||
| 1995 | L Fletcher | Poynton Sports | |
| 1994 | G Davies | Winsford | |
| 1993 | N Whiston | Shavington | |
| 1992 | P Jones | Chester | |
| 1991 | S Mathias | Ellesmere Port | |
| 1990 | M Vernon | Winsford | |
| Year | Winner | Club | |
| 1989 | M Ogiliev | Altrincham | |
| 1988 | G Foster | Macclesfield |