Fosters Fife Cup Round 1
 AM Soccer AFC   1 v 3  Greig Park Rangers AFC
 Bowhill Rovers AFC   13 v 1  Glenrothes Athletic AFC
 Hearts of Beath AFC  12 v 0  Kelty Hearts AFC
 Kingdom Athletic AFC   1 v 3  Fossoway AFC
 Strathmiglo United AFC   1 v 3  Cupar Hearts AFC
 AM Soccer Reserves AFC   2 v 3  Kirkcaldy Rovers AFC
 Glenrothes AFC   1 v 2  Newport AFC
 Leslie Hearts AFC   3 v 2  Balgonie Scotia AFC
Fosters Fife Cup Round 2
 Cupar Hearts AFC   3 v 0  St Monans Swallows AFC
 Glenrothes Strollers AFC   1 v 1  Burntisland United AFC
 Kinross Colts AFC   2 v 7  Newport AFC
 Auchtermuchty Bellvue AFC   6 v 1  Fife Thistle AFC
 Kirkcaldy AFC   4 v 1  Lomond Victoria AFC
 Rosebank AFC   1 v 5  Greig Park Rangers AFC
 Rosyth AFC   1 v 4  Aberdour AFC
 St Andrews AFC   2 v 5  Hearts of Beath AFC
 FC Bayside AFC   4 v 2  Leslie Hearts AFC
 Bowhill Rovers AFC   6 v 3  Pittenweem Rovers AFC
 Denbeath AFC   1 v 4  Lumphinnans United AFC
 Fossoway AFC   4 v 0  Kirkland Villa AFC
 Freuchie AFC   3 v 2  Falkland AFC
 Kinglassie AFC   2 v 3  Kirkcaldy Rovers AFC
 Methilhill Strollers AFC   1 v 2  Leven United AFC
 Bye      v  Kirkcaldy YMCA AFC
Fosters Fife Cup Round 3
Aberdour AFC  3 v  2 Glenrothes Strollers AFC
Bowhill Rovers AFC  7 v 3 Hearts of Beath AFC
Cupar Hearts AFC  1 v 2 Auchtermuchty Bellvue AFC
FC Bayside AFC  7 v 8 Newport AFC
Freuchie AFC  0 v 7 Greig Park Rangers AFC
Kirkcaldy AFC  1 v 2 Lumphinnans United AFC
Kirkcaldy YMCA AFC  6 v 1 Kirkcaldy Rovers AFC
Leven United AFC   4 v 1 Fossoway AFC
Fosters Fife Cup Quarters
 Aberdour AFC    2 v 1  Kirkcaldy YMCA AFC
 Leven United AFC    9 v 2  Auchtermuchty Bellvue AFC
 Bowhill Rovers AFC    7  v 2  Newport AFC
 Lumphinnans United AFC    1  v 4  Greig Park Rangers AFC
Fosters Fife Cup Semis
 Aberdour AFC   1 v 2  Greig Park Rangers AFC
 Leven United AFC  Bowhill Rovers AFC
Fosters Fife Cup Final
 Greig Park Rangers AFC  6-7p  Leven United AFC

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Previous Winners
1931-1932 Burntisland Shipyard
1932-1933 Bishopshire Swifts
1933-1934 Glencraig Victoria
1934-1935 St Andrews University
1935-1936 Crail
1936-1937 Pittenweem Rovers
1937-1938 Freuchie Rovers
1938-1939 Pittenweem Rovers
1945-1946 Burntisland Shipyard
1946-1947 Gallatown YMCA
1947-1948 Milton Violet
1948-1949 Victoria Swifts
1949-1950 Boreland
1950-1951 Ladybank Violet
1951-1952 Ladybank Violet
1952-1953 Boreland
1953-1954 Thornton Loco
1954-1955 Thornton Loco
1955-1956 Boreland
1956-1957 Thornton Loco
1957-1958 St Andrews University
1958-1959 Cupar YMCA
1959-1960 Westwood Wanderers
1960-1961 Nairn Star
1961-1962 Westwood Wanderers
1962-1963 Nairn Star
1963-1964 St Monans Swallows
1964-1965 St Monans Swallows
1965-1966 Cambusbarron Rovers
1966-1967 Cambusbarron Rovers
1967-1968 Star Hearts
1968-1969 Star Hearts
1969-1970 Star Hearts
1970-1971 Star Hearts
1971-1972 St Monans Swallows
1972-1973 Methil United
1973-1974 Star Hearts
1974-1975 Star Hearts
1975-1976 Star Hearts
1976-1977 Hill of Beath Hawthorn
1977-1978 Windygates
1978-1979 Star Hearts
1979-1980 Windygates
1980-1981 Norton House
1981-1982 Strathmiglo United
1982-1983 Star Hearts
1983-1984 Norton House
1984-1985 Ballingry Rovers
1985-1986 Strathmiglo United
1986-1987 Norton House
1987-1988 Hill of Beath Ramblers
1988-1989 Norton House
1989-1990 Burntisland Shipyard
1990-1991 Star Hearts
1991-1992 Burntisland Shipyard
1992-1993 Norton House
1993-1994 Benarty
1994-1995 Benarty
1995-1996 Kettle United
1996-1997 Burntisland Shipyard
1997-1998 Lomond Victoria
1998-1999 Leven United
1999-2000 Norton House
2000-2001 Norton House
2001-2002 Norton House
2002-2003 Norton House
2003-2004 Valleyfield
2004-2005 Kettle United
2005-2006 Kirkland AFC
2006-2007 Cupar Hearts
2007-2008 Cupar Hearts
2008-2009 Strathmiglo United
2009-2010 Cupar Hearts
2010-2011 Cupar Hearts
2011-2012 Kennoway
2012-2013 Leven United
2013-2014 Bowhill Rovers
2014-2015 Pittenweem Rovers
2015-2016 Pittenweem Rovers
2016-2017 Leven United