County Handicap History
| Year | Winner | Club | Runner-up | Club | Clare Cup | Club |
|---|---|---|---|---|---|---|
| 2025 | A. Wellings | Castlefields | C. Elsbury | Prince of Wales Hotel | E. Hotchkiss | Prince of Wales Hotel |
| 2024 | C. Wraight | Castlefields | S. Harries | Bylet | E. McKinley | Oxon |
| 2023 | S. Moseley | Wrockwardine Wood | A. Rowe | Castlefields | J. Cotterill | Newport |
| 2022 | A. Purcell | Chester Road | J. Mansell | Hanwood | T. Killen | Shifnal |
| 2021 | C. Wraight | Castlefields | B. Hinton | Chester Road | C. Wilkinson | AWC |
| 2020 | NOT HELD | |||||
| 2019 | S O’Nions | Telepost | J. Bradburn | Newport | B. Hinton | District |
| 2018 | D. Wornell | Hanwood | J. Hewitt | Hanmer | J. Hewitt | Hanmer |
| 2017 | R. Lawson | Bowring | S. Simpson | Sir John Bayley | H. Parsonage | Burway |
| 2016 | R. Lawson | Bowring | M. Beer | Castlefields | C. Elsbury | Hadnall |
| 2015 | R. Lawson | Bowring | Doug Edwards | Meole Brace | Dan Beer | Battlefield |
| 2014 | M. Beer | Castlefields | Doug Edwards | Prince of Wales | D. Powis | Old Shrewsbury |
| 2013 | M. Beer | Castlefields | J. Austin | Castlefields | J. Austin | Castlefields |
| 2012 | A. Rowe | Meole Brace | P. Grimston | Sir John Bayley | D. Ashley | Reman |
| 2011 | M. Beer | Castlefields | A. Duckett | Chester Road | D. Renwick | Unison |
| 2010 | K. Wall | Castlefields | C. Weaver | Chester Road | J. Farmer | Childs Ercall |
| 2009 | P. Farmer | St Georges | P. King | Hadley USC | D. Williams | Reman Services |
| 2008 | A. Moss | Chester Road | Daryl Edwards | Pontesbury | J. King | Hadley U.S.C. |
| 2007 | S. Leslie | Reman | M. Beer | Castlefields | S. Leslie | Reman |
| 2006 | Colin Beaman | Meole Brace | M. Holland | Chester Road | B. Hickson | Prees |
| 2005 | M. Lloyd | District | T. Hotchkiss | Ford | ||
| 2004 | A. Moss | Chester Road | K. Wall | Castlefields | J.E. Davies | Monkmoor |
| 2003 | M. Lloyd | District | K. Price | Castlefields | A. Marshal | Castlefields |
| 2002 | K. Wall | Battlefield | P. Smith | Archibald Worthington | N. Ferrington | Bricklayers |
| 2001 | T. Dodd | Meole Brace | T. Lewis | Greenfields | ||
| 2000 | P. Whatmough | Castlefields | P. Latham | Woore | A. Boycott | Donnington Wood |
| 1999 | Colin Beaman | Battlefield | P. Farmer | Childs Ercall | C. Worthington | Donnington Wood |
| 1998 | M. Jones | St Georges | T. Gray | Battlefield | J. Grenville | Perkins |
| 1997 | P. Williams | Castlefields | T. Cutting | Craven Arms | R. Addison | Royal Mail |
| 1996 | P. Williams | Castlefields | P. Farmer | Hadley USC | D. Hoffman | Ford |
| 1995 | D. Wright | Wem U.S.C. | C. Ball | St Georges | D. Walton | Pontesbury |
| 1994 | P. Smith | Corbet-Market Drayton | D. Phillips | Hanwood | ||
| 1993 | A. Wigginton | Meole Brace | A. Stephens | Pontesbury | C. Jones | POWBC |
| 1992 | D. Wright | Wem U.S.C. | P. Farmer | Four Crosses | C. Bowers | Hanwood |
| 1991 | K. Walton | Meole Brace | A.F. Poole | Castlefields | J. Emonson | Coddon |
| 1990 | K. Walton | Meole Brace | P. Farmer | Four Crosses | R. Hyne | Ford |
| 1989 | G. Herbert | Castlefields | I.D. Gaut | Wrockwardine Wood | P. Clee | Wrockwardine Wood |
| 1988 | K. Jones | Ford | G. Davies | Ford | P. Smith | Corbet |
| 1987 | A.F. Poole | Castlefields | A.D. Gaut | Donnington Wood | A. Dowley | Wem U.S.C. |
| 1986 | W. Phillips | Hanwood | P. Bound | Battlefield | W. France | Charlton |
| 1985 | A. Dodd | Oxon | P. Bound | Battlefield | D. Ruscoe | Springfield |
| 1984 | E. Jones | Pontesbury | S. Parsonage | Ludlow Castle | D. King | Cock Hotel |
| 1983 | A.F. Poole | Castlefields | N. Bound | Ford | G. Wall | Castlefields |
| 1982 | W.T.P. Sambrook | Severnside | G. Lovatt | Dun Cow | M. Potter | Corporation |
| 1981 | A.F. Poole | Castlefields | D. Hill | Castlefields | P. Walker | Castlefields |
| 1980 | S. Williams | Pontesbury | R. Cliffe | Meole Brace | A. Dodd | Oxon |
| 1979 | C. Ball | St Georges | D. Downes | G.K.N. Sankey | D.A. Downes | G.K.N. Sankey |
| 1978 | A.D. Gaut | Donnington Wood | I.D. Gaut | Donnington Wood | I. Gaut | Donnington Wood |
| 1977 | C. Lewis | Glynwed | R. Bond | St Georges | A.D. Jones | G.K.N. Sankey |
| 1976 | Clive Beaman | Telepost | R. Clarke | Sir John Bayley | B. Gowes | St. Julians |
| 1975 | K. Walton | Meole Brace | M.W. Codd | Castlefields | M. Breakell | St. Julians |
| 1974 | A.F. Poole | Castlefields | G.A. Gaut | Donnington Wood | M.J. Williams | Telepost |
| 1973 | G. Adams | Meole Brace | M. Meredith | Crescent | P. Bound | Ford |
| 1972 | W.T.P. Sambrook | Severnside | H. Smale | Monkmoor | C.A. Bancroft | Rolls Royce |
| 1971 | W.T.P. Sambrook | Severnside | E. James | Wrockwardine Wood | J. Rogers | Rolls Royce |
| 1970 | C. Rushton | Battlefield | P. Youens | Ye Olde Crofte | G.A. Riley | Donnington Wood |
| 1969 | G. Edmunds | Bylet | D.M. Beer | Battlefield | G. Griffiths | St. Julians |
| 1968 | C. Rushton | St Julians | Clive Beaman | Postal | D. Pritchard | Monkmoor |
| 1967 | R. Bourne | Battlefield | D.M. Beer | Battlefield | B. Keep | Castlefields |
| 1966 | D.I. Lawrence | Pontesbury | P.A. Beech | Meole Brace | C.T. Lewis | Meole Brace |
| 1965 | B. Mansell | Battlefield | J. Bradick | Castlefields | J.R. Alcock | Horsehay |
| 1964 | D.I. Lawrence | Pontesbury | J. Lewis | Meole Brace | J.H. Lewis | Meole Brace |
| 1963 | D.M. Beer | Battlefield | D. Croft | Ditherington | Dave M. Beer | Battlefield |
| 1962 | D. Turner | Bylet | J.E. Tipton | Crescent | ||
| 1961 | T.L. Potter | Meole Brace | E.W.G. Stephens | Pontesbury | ||
| 1960 | A.E. Jones | St Julians | D.I. Lawrence | Pontesbury | ||
| 1959 | A. Thomas | Castlefields | D.I. Lawrence | Pontesbury | ||
| 1958 | D.I. Lawrence | Pontesbury | C. Palmer | Bylet | ||
| 1957 | W.S. Genoe | Postal | T. Candlin | Allied Ironfounders | ||
| 1956 | D.I. Lawrence | Pontesbury | W.E. Evans | Crescent | ||
| 1955 | R.G. Meyrick | N.A.L.G.O | R.S. Thomas | Castlefields | ||
| 1954 | W.C. Twyford | Castlefields | A.R. Jones | Wrockwardine Wood | ||
| 1953 | ||||||
| 1952 | R.S. Thomas | Castlefields | R. Thomas | Castlefields | ||
| 1951 | W. Jones | Malpas | R. Thomas | Castlefields | ||
| 1950 | N. Phillips | Monkmoor | R.R. Lloyd | Sir John Bayley | ||
| 1949 | W.C. Twyford | Castlefields | R.S. Thomas | Ditherington | ||
| 1948 | R. Thomas | Castlefields | D. Isherwood | Meole Brace | ||
| 1947 | R.G. Meyrick | N.A.L.G.O | F. Payne | Sir John Bayley | ||
| 1946 | L.A. Page | Meole Brace | J. James | Battlefield | ||
| 1945 | A. Thomas | Monkmoor | R. Thomas | Monkmoor | ||
| 1944 | R.G. Meyrick | N.A.L.G.O | R. Thomas | Monkmoor | ||
| 1943 | No Competition | |||||
| 1942 | No Competition | |||||
| 1941 | No Competition | |||||
| 1940 | No Competition | |||||
| 1939 | J. Candlin | Charlton | J. Williams | Roden | ||
| 1938 | R. Thomas | Roden | F. Capes | Hadley Kings Head | ||
| 1937 | W.J. Gennoe | Postal | S.C. Galley | All Saints | ||
| 1936 | S.C. Galley | All Saints | I.B. Jones | N.A.L.G.O | ||
| 1935 | F. Hilton | Sentinel | A. Thomas | Monkmoor | ||
| 1934 | R.G. Meyrick | N.A.L.G.O | P. Owen | Greenfields | ||
| 1933 | W.M. Howells | All Saints | R. Thomas | Roden | ||
| 1932 | A. Rowlinson | Chatwood | T. Irving | Monkmoor | ||
| 1931 | C. Morris | Sentinel | R. Lambert | Borough Police | ||
| 1930 | C. Evans | Dawley | W.J. Gennoe | All Saints | ||
| 1929 | W.J. Lokier | All Saints | A. Riley | Charlton | ||
| 1928 | W. Dinwoodie | Severnside | R. Rees | Uffington | ||
| 1927 | A. Riley | Cock Hotel | W. Dinwoodie | Severnside | ||
| 1926 | W.A. Hewitt | Severnside | A. Shand | Battlefield | ||
| 1925 | J.H. Pye | Severnside | W.A. Hewitt | Severnside | ||
| 1924 | C. Magness | Cock Hotel | J. Jones | Severnside | ||
| 1923 | A. Lloyd | Cock Hotel | H. Bess | Roden | ||
| 1922 | J. Jones | Severnside | W.A. Hewitt | Severnside | ||
| 1921 | S.T. Carlisle | Old Shrewsbury | W.A. Hewitt | Severnside | ||
| 1920 | H.E. Gunn | Church Stretton | E.T. Davies | Belgrave | ||
| 1919 | E.T. Jones | Old Shrewsbury | W.A. Parton | Oakengates | ||
| 1918 | E.T. Davies | Belgrave | W.A. Hewitt | Severnside |
