The County Cup has been played for since 1921 for the Glynn Hill Trophy. The record winners are Castlefields with 23 triumphs, with Bowring being the holders.
| Year | Winner | Runner-up |
| 2016 | Bowring | Castlefields |
| 2015 | Castlefields | Meole Brace |
| 2014 | Newport | Burway |
| 2013 | Sir John Bayley | Newport |
| 2012 | Newport | Chester Road |
| 2011 | Chester Road | Newport |
| 2010 | St Georges | Ford |
| 2009 | Chester Road | Castlefields |
| 2008 | Castlefields | St Georges |
| 2007 | Chester Road | Wem United Services |
| 2006 | Sir John Bayley | St Georges |
| 2005 | Chester Road | Meole Brace |
| 2004 | Castlefields | Ford |
| 2003 | Chester Road | Meole Brace |
| 2002 | Castlefields | Ifton |
| 2001 | St Georges | Wrockwardine Wood |
| 2000 | Castlefields | Chester Road |
| 1999 | St Georges | Chester Road |
| 1998 | St Georges | Chester Road |
| 1997 | Castlefields | Wem United Services |
| 1996 | Castlefields | St Georges |
| 1995 | Castlefields | St Georges |
| 1994 | Chester Road | St Georges |
| 1993 | Castlefields | Wem United Services |
| 1992 | St Georges | Castlefields |
| 1991 | Meole Brace | Castlefields |
| 1990 | St Georges | Hanwood |
| 1989 | Castlefields | Meole Brace |
| 1988 | Castlefields | Hanwood |
| 1987 | Donnington Wood | St Georges |
| 1986 | Donnington Wood | St Georges |
| 1985 | Meole Brace | Wrockwardine Wood |
| 1984 | Battlefield | Castlefields |
| 1983 | Castlefields | Meole Brace |
| 1982 | Meole Brace | Castlefields |
| 1981 | Hadley United Services Club | Crescent |
| 1980 | St Georges | Hadley United Services |
| 1979 | Meole Brace | G.K.N. Sankey |
| 1978 | Hadley United Services Club | Castlefields |
| 1977 | St Georges | Battlefield |
| 1976 | Battlefield | Castlefields |
| 1975 | Battlefield | Meole Brace |
| 1974 | Crescent | Battlefield |
| 1973 | Meole Brace | Battlefield |
| 1972 | St Georges | Battlefield |
| 1971 | Glynwed | Meole Brace |
| 1970 | Battlefield | Sir John Bayley |
| 1969 | Battlefield | Crescent |
| 1968 | Crescent | Castlefields |
| 1967 | Castlefields | Meole Brace |
| 1966 | Castlefields | Battlefield |
| 1965 | Castlefields | Hadley United Services |
| 1964 | Sir John Bayley and Wrockwardine Wood (TIE) | |
| 1963 | Castlefields | Pontesbury |
| 1962 | Meole Brace | Severnside |
| 1961 | Castlefields | Meole Brace |
| 1960 | Castlefields | Pontesbury |
| 1959 | Castlefields | St Georges |
| 1958 | Castlefields | Pontesbury |
| 1957 | Crescent | St Georges |
| 1956 | Sankeys Works | Castlefields |
| 1955 | Castlefields | Dun Cow, Dawley |
| 1954 | N.A.L.G.O | Trench |
| 1953 | Sentinel | Castlefields |
| 1952 | N.A.L.G.O | Wrockwardine Wood |
| 1951 | Castlefields | N.A.L.G.O |
| 1950 | N.A.L.G.O | Castlefields |
| 1949 | N.A.L.G.O | Trench |
| 1948 | Sir John Bayley | Dun Cow, Dawley |
| 1947 | N.A.L.G.O | Postal |
| 1946 | Royal Exchange | Frankwell |
| 1945 | Postal | Trench |
| 1944 | Old Shrewsbury | Sir John Bayley |
| 1943 | St Georges | Monkmoor |
| 1942 | Castlefields | Hadley Kings Head |
| 1941 | Trench | Monkmoor |
| 1940 | Old Shrewsbury | Trench |
| 1939 | St Georges | Roden |
| 1938 | Frankwell | Postal |
| 1937 | Postal | Ford |
| 1936 | Battlefield | Cae Glas |
| 1935 | Horsehay Works | All Saints |
| 1934 | Royal Exchange | Roden |
| 1933 | Cock Hotel and Severnside (TIE) | |
| 1932 | Cock Hotel | Frankwell |
| 1931 | Old Shrewsbury | Royal Exchange |
| 1930 | Belgrave | Horsehay Works |
| 1929 | Severnside | All Saints |
| 1928 | Belgrave | Hadley Castle |
| 1927 | Greenfields | Frankwell |
| 1926 | Severnside | Dawley B.C. |
| 1925 | Severnside | Belgrave |
| 1924 | Old Shrewsbury | Greenfields |
| 1923 | Belgrave | Cock Hotel |
| 1922 | Belgrave | Old Shrewsbury |
| 1921 | Old Shrewsbury | Islington |
