Chester & District League Winners - Division 1
| Season Start | Season End | Winner |
|---|---|---|
| 1954 | 1955 | YMCA |
| 1955 | 1956 | YMCA |
| 1956 | 1957 | YMCA |
| 1957 | 1958 | YMCA |
| 1958 | 1959 | Wrexham |
| 1959 | 1960 | YMCA A |
| 1960 | 1961 | YMCA Knights |
| 1961 | 1962 | Capenhurst |
| 1962 | 1963 | Deeside |
| 1963 | 1964 | YMCA 1 |
| 1964 | 1965 | YMCA 1 |
| 1965 | 1966 | YMCA 1 |
| 1966 | 1967 | YMCA 1 |
| 1967 | 1968 | Capenhurst |
| 1968 | 1969 | Capenhurst |
| 1969 | 1970 | Capenhurst |
| 1970 | 1971 | Capenhurst |
| 1971 | 1972 | Mynnd Isa |
| 1972 | 1973 | Rhyl |
| 1973 | 1974 | YMCA 1 |
| 1974 | 1975 | YMCA 1 |
| 1975 | 1976 | YMCA 1 |
| 1976 | 1977 | YMCA 1 |
| 1977 | 1978 | YMCA 1 |
| 1978 | 1979 | Wallasey |
| 1979 | 1980 | YMCA 1 |
| 1980 | 1981 | YMCA Rooks |
| 1981 | 1982 | Wrexham |
| 1982 | 1983 | East Clywd |
| 1983 | 1984 | YMCA Knights |
| 1984 | 1985 | YMCA Knights |
| 1985 | 1986 | YMCA Knights |
| 1986 | 1987 | Wrexham |
| 1987 | 1988 | YMCA |
| 1988 | 1989 | YMCA Knights |
| 1989 | 1990 | Wrexham |
| 1990 | 1991 | Wrexham |
| 1991 | 1992 | Wrexham |
| 1992 | 1993 | Rhyl |
| 1993 | 1994 | Wrexham |
| 1994 | 1995 | Wrexham |
| 1995 | 1996 | Wrexham |
| 1996 | 1997 | Ruthin |
| 1997 | 1998 | Llandudno |
| 1998 | 1999 | Llandudno |
| 1999 | 2000 | YMCA |
| 2000 | 2001 | Wrexham |
| 2001 | 2002 | Wrexham |
| 2002 | 2003 | Wrexham |
| 2003 | 2004 | Chester YMCA |
| 2004 | 2005 | Wrexham |
| 2005 | 2006 | Chester |
| 2006 | 2007 | Chester 1 |
| 2007 | 2008 | Caergwrle |
| 2008 | 2009 | Wrexham |
| 2009 | 2010 | Wrexham |
| 2010 | 2011 | Wrexham |
| 2011 | 2012 | Chester 1 |
| 2012 | 2013 | Wrexham |
| 2013 | 2014 | Chester 1 |
| 2014 | 2015 | Wrexham |
| 2015 | 2016 | Chester 1 |
| 2016 | 2017 | Chester 1 |
| 2017 | 2018 | Chester 1 |
| 2018 | 2019 | Chester 1 |
Chester & District League Winners - Division 2
| Season Start | Season End | Winner |
|---|---|---|
| 1960 | 1961 | Capenhurst |
| 1961 | 1962 | Mold |
| 1962 | 1963 | Bowaters |
| 1963 | 1964 | Wrexham 2 |
| 1964 | 1965 | Northwich 1 |
| 1965 | 1966 | Wrexham 2 |
| 1966 | 1967 | YMCA 2 |
| 1967 | 1968 | Deeside 2 |
| 1968 | 1969 | Shell |
| 1969 | 1970 | Wrexham 2 |
| 1970 | 1971 | Kings School |
| 1971 | 1972 | Shell |
| 1972 | 1973 | Mynydd Isa |
| 1973 | 1974 | Wrexham 2 |
| 1974 | 1975 | YMCA 2 |
| 1975 | 1976 | Wrexham 2 |
| 1976 | 1977 | Wallasey |
| 1977 | 1978 | Capenhurst |
| 1978 | 1979 | Rhyl 2 |
| 1979 | 1980 | Mold |
| 1980 | 1981 | Wallasey |
| 1981 | 1982 | Shell |
| 1982 | 1983 | Vauxhall 2 |
| 1983 | 1984 | Wrexham 3 |
| 1984 | 1985 | Colwyn Bay |
| 1985 | 1986 | Rhyl 2 |
| 1986 | 1987 | Shell |
| 1987 | 1988 | Vauxhall |
| 1988 | 1989 | Capenhurst 2 |
| 1989 | 1990 | Shell |
| 1990 | 1991 | Ruthin |
| 1991 | 1992 | Capenhurst 2 |
| 1992 | 1993 | Ruthin |
| 1993 | 1994 | Buckley |
| 1994 | 1995 | Buckley |
| 1995 | 1996 | Rhyl Hawks |
| 1996 | 1997 | Buckley |
| 1997 | 1998 | Frodsham |
| 1998 | 1999 | Rhyl G. K. |
| 1999 | 2000 | YMCA |
| 2000 | 2001 | Buckley Mold |
| 2001 | 2002 | Wrexham |
| 2002 | 2003 | Colwyn Bay |
| 2003 | 2004 | Llandudno |
| 2004 | 2005 | Colwyn Bay |
| 2005 | 2006 | Chester 2 |
| 2006 | 2007 | Chester 3 |
| 2007 | 2008 | Capenhurst |
| 2008 | 2009 | Chester 3 |
| 2009 | 2010 | Buckley Mold |
| 2010 | 2011 | Colwyn Bay |
| 2011 | 2012 | Chester 4 |
| 2012 | 2013 | Chester 4 |
| 2013 | 2014 | Buckley Mold |
| 2014 | 2015 | Wrexham (E) Penyffordd (W) |
| 2015 | 2016 | Malpas & Whitchurch |
| 2016 | 2017 | Chester 4 |
| 2017 | 2018 | Wrexham 2 |
| 2018 | 2019 | Chester 4 |
Chester & District League Winners - Division 3
| 1963 | 1964 | Northwich |
| 1964 | 1965 | Shell |
| 1965 | 1966 | |
| 1966 | 1967 | |
| 1967 | 1968 | |
| 1968 | 1969 | |
| 1969 | 1970 | |
| 1970 | 1971 | |
| 1971 | 1972 | |
| 1972 | 1973 | |
| 1973 | 1974 | Manweb |
| 1974 | 1975 | Wrexham 3 |
| 1975 | 1976 | Vauxhall 2 |
| 1976 | 1977 | Rhyl 3 |
| 1977 | 1978 | Queens Park High |
| 1978 | 1979 | ICI |
| 1979 | 1980 | East Clwyd |
| 1980 | 1981 | Shell |
| 1981 | 1982 | Rhyl 3 |
| 1982 | 1983 | College of Law |
| 1983 | 1984 | Mold |
| 1984 | 1985 | YMCA |
| 1985 | 1986 | Frodsham 2 |
| 1986 | 1987 | Rhyl 3 |
| 1987 | 1988 | YMCA |
| 1988 | 1989 | Rhyl 3 |
| 1989 | 1990 | Ruthin |
| 1990 | 1991 | Vauxhall |
| 1991 | 1992 | Colwyn Bay |
| 1992 | 1993 | Rhyl Bishops |
| 1993 | 1994 | Kings School |
| 1994 | 1995 | Rhyl 3 |
| 1995 | 1996 | Llandudno 2 |
| 1996 | 1997 | YMCA |
| 1997 | 1998 | Caergwrle |
| 1998 | 1999 | Capenhurst 2 |
| 1999 | 2000 | Ruthin 2 |
| 2000 | 2001 | Colwyn Bay |
| 2001 | 2002 | Capenhurst |
| 2002 | 2003 | Rhyl 2 |
| 2003 | 2004 | Buckley Mold |
| 2004 | 2005 | Chester 4 |
| 2005 | 2006 | Rhyl 2 |
| 2006 | 2007 | Chester 5 |
| 2007 | 2008 | Buckley Mold 2 |
| 2008 | 2009 | Chester 4 |
| 2009 | 2010 | Buckley Mold 2 |
| 2010 | 2011 | Wrexham |
| 2011 | 2012 | Wrexham |
| 2012 | 2013 | Carden Arms |
| 2013 | 2014 | Colwyn Bay 3 |
| 2014 | 2015 | Rhyl & Prestatyn |
| 2015 | 2016 | Holywell Knights |
| 2016 | 2017 | Chester 6 |
| 2017 | 2018 | Malpas & Oswestry 2 |
| 2018 | 2019 | Holywell Knights |
Chester & District League Winners - Knock out
| Year | Winner |
|---|---|
| 1961 | Chester YMCA |
| 1962 | Capenhurst |
| 1963 | Capenhurst |
| 1964 | YMCA |
| 1965 | Northwich |
| 1966 | Chester YMCA |
| 1967 | Kings School |
| 1968 | Northwich |
| 1969 | Kings School |
| 1970 | Chester YMCA |
| 1971 | Capenhurst |
| 1972 | Wrexham |
| 1973 | Manweb |
| 1974 | Wrexham |
| 1975 | Rhyl |
| 1976 | Rhyl |
| 1977 | Chester YMCA |
| 1978 | Chester YMCA |
| 1979 | Rhyl |
| 1980 | Queens Park High School |
| 1981 | Wrexham |
| 1982 | Wrexham |
| 1983 | Chester YMCA |
| 1984 | East Clywd |
| 1985 | East Clywd |
| 1986 | Wrexham |
| 1987 | YMCA Chester |
| 1988 | YMCA Chester |
| 1989 | Wrexham |
| 1990 | Rhyl |
| 1991 | Wrexham |
| 1992 | Wrexham |
| 1993 | YMCA Chester |
| 1994 | Wrexham |
| 1995 | Wrexham |
| 1996 | Wrexham |
| 1997 | Wrexham |
| 1998 | Llandudno |
| 1999 | Wrexham |
| 2000 | Northgate Church |
| 2001 | Wrexham |
| 2002 | Caergwrle |
| 2003 | Wrexham |
| 2004 | Wrexham |
| 2005 | Wrexham |
| 2006 | Chester |
| 2007 | Holywell |
| 2008 | Holywell |
| 2009 | Wrexham |
| 2010 | Wrexham |
| 2011 | Wrexham |
| 2012 | Wrexham |
| 2013 | Wrexham |
| 2014 | Chester |
| 2015 | Wrexham |
| 2016 | Malpas & Whitchurch |
| 2017 | Chester |
| 2018 | Chester |
| 2019 | Chester |