Scottish League Cup 2023/24, Group G |
 | 29.07.2023 | | Motherwell | – | East Fife | | 3:0 (2:0) |
| Motherwell |
Scottish League Cup 2022/23, Group C |
| 23.07.2022 | | Ross County | – | East Fife | | 7:0 (2:0) |
| Dingwall |
Scottish League Cup 2022/23, Group C |
| 09.07.2022 | | East Fife | – | Dunfermline Athletic | | 0:2 (0:0) |
| Methil |
Scottish League Cup 2021/22, Group B |
| 24.07.2021 | | East Fife | – | Elgin City | | 2:3 (2:2) |
| Methil |
Scottish League Cup 2021/22, Group B |
| 20.07.2021 | | East Fife | – | Dundee United | | 0:1 (0:1) |
| Methil |
Scottish League Cup 2021/22, Group B |
| 17.07.2021 | | Kelty Hearts | – | East Fife | | 3:0 (2:0) |
| Kelty |
Scottish League Cup 2021/22, Group B |
| 14.07.2021 | | Arbroath | – | East Fife | | 2:0 (0:0) |
| Arbroath |
Scottish League Cup 2020/21, Group A |
| 14.11.2020 | | Inverness | – | East Fife | | 1:0 (0:0) |
| Inverness |
Scottish League Cup 2020/21, Group A |
| 10.11.2020 | | East Fife | – | Hearts | | 2:3 (1:2) |
| Methil |
Scottish League Cup 2020/21, Group A |
| 10.10.2020 | | Raith Rovers | – | East Fife | | 2:1 (1:1) |
| Kirkcaldy |
Scottish League Cup 2019/20, Second round |
| 18.08.2019 | | East Fife | – | Rangers | | 0:3 (0:1) |
| Methil |
Scottish League Cup 2019/20, Group A |
| 13.07.2019 | | Cowdenbeath | – | East Fife | | 2:0 (2:0) |
| Cowdenbeath |
Scottish League Cup 2018/19, Group B |
| 28.07.2018 | | East Fife | – | Falkirk | | 1:2 (1:0) |
| Methil |
Scottish League Cup 2018/19, Group B |
| 17.07.2018 | | Montrose | – | East Fife | | 1:0 (0:0) |
| Montrose |
Scottish League Cup 2017/18, Group B |
| 22.07.2017 | | Hearts | – | East Fife | | 3:0 (1:0) |
| Edinburgh |
Scottish League Cup 2017/18, Group B |
| 15.07.2017 | | Peterhead | – | East Fife | | 1:0 (1:0) |
| Peterhead |
Scottish League Cup 2016/17, First Round, Group A |
| 26.07.2016 | | Forfar Athletic | – | East Fife | | 2:0 (1:0) |
| Forfar |
Scottish League Cup 2015/16, Second Round |
| 25.08.2015 | | East Fife | – | Motherwell | | 1:3 aet
(0:0, 1:1) |
| Methil |
Scottish League Cup 2014/15, First Round |
| 02.08.2014 | | Stranraer | – | East Fife | | 1:0 (0:0) |
| Stranraer |
Scottish League Cup 2013/14, First Round |
| 03.08.2013 | | East Fife | – | Greenock Morton | | 2:6 aet
(0:0, 2:2) |
| Methil |
Scottish League Cup 2012/13, First Round |
| 07.08.2012 | | Rangers | – | East Fife | | 4:0 (2:0) |
| Glasgow |
Scottish League Cup 2011/12, Quarterfinal |
| 25.10.2011 | | Kilmarnock | – | East Fife | | 2:0 (0:0) |
| Kilmarnock |
Scottish League Cup 2010/11, First Round |
| 31.07.2010 | | Raith Rovers | – | East Fife | | 4:1 (3:0) |
| Kirkcaldy |
Scottish League Cup 2009/10, First Round |
| 01.08.2009 | | East Fife | – | Raith Rovers | | 2:3 (2:0) |
| Methil |
Scottish League Cup 2008/09, First Round |
| 06.08.2008 | | East Fife | – | Brechin City | | 0:3 (0:1) |
| Methil |
Scottish League Cup 2007/08, Third Round |
| 26.09.2007 | | East Fife | – | Rangers | | 0:4 (0:2) |
| Dunfermline |
Scottish League Cup 2006/07, First Round |
| 08.08.2006 | | St. Johnstone | – | East Fife | | 3:1 (0:0) |
| Perth |
Scottish League Cup 2005/06, First Round |
| 09.08.2005 | | East Fife | – | Stranraer | | 0:1 (0:0) |
| |
Scottish League Cup 2004/05, First Round |
| 10.08.2004 | | Airdrie United | – | East Fife | | 3:0 (2:0) |
| |
Scottish League Cup 2003/04, First Round |
| 02.09.2003 | | East Fife | – | Airdrie United | | 0:2 (0:1) |
| |
Scottish League Cup 2002/03, Second Round |
| 24.09.2002 | | East Fife | – | Motherwell | | 0:2 (0:1) |
| |
Scottish League Cup 2001/02, Second Round |
| 26.09.2001 | | Livingston | – | East Fife | | 3:0 |
| |
Scottish League Cup 2000/01, First Round |
| 08.08.2000 | | East Fife | – | Raith Rovers | | 1:2 |
| |
Scottish League Cup 1999/00, Third Round |
| 12.10.1999 | | East Fife | – | Hearts | | 0:2 |
| |
Scottish League Cup 1998, Second Round |
| 08.08.1998 | | East Fife | – | Motherwell | | 0:1 |
| |
Scottish League Cup 1997, Second Round |
| 09.08.1997 | | East Fife | – | Kilmarnock | | 0:2 |
| |
Scottish League Cup 1996, Second Round |
| 13.08.1996 | | East Fife | – | St. Johnstone | | 1:5 |
| |
Scottish League Cup 1995, Second Round |
| 19.08.1995 | | East Fife | – | Airdrieonians | | 2:3 |
| |
Scottish League Cup 1994, Second Round |
| 17.08.1994 | | Kilmarnock | – | East Fife | | 4:1 |
| |
Scottish League Cup 1993, First Round |
| 03.08.1993 | | East Fife | – | Albion Rovers | | 1:2 |
| |
Scottish League Cup 1985, Second Round |
| 20.08.1985 | | Hamilton Academical | – | East Fife | | 2:0 |
| |
Scottish League Cup 1984, Second Round |
| 21.08.1984 | | Hibernian | – | East Fife | | 1:0 |
| |
Scottish League Cup 1983/84, Second Round |
| 27.08.1983 | | St. Johnstone | – | East Fife | | 6:3 |
| |
Scottish League Cup 1983/84, Second Round |
| 24.08.1983 | | East Fife | – | St. Johnstone | | 1:2 |
| |
Scottish League Cup 1982, Group 7 |
| 28.08.1982 | | Brechin City | – | East Fife | | 4:0 |
| |
Scottish League Cup 1982, Group 7 |
| 25.08.1982 | | East Fife | – | Partick Thistle | | 0:3 |
| |
Scottish League Cup 1982, Group 7 |
| 21.08.1982 | | East Fife | – | East Stirlingshire | | 0:1 |
| |
Scottish League Cup 1981, Group 9 |
| 15.08.1981 | | East Fife | – | Meadowbank Thistle | | 0:1 |
| |
Scottish League Cup 1980, First Round |
| 20.08.1980 | | Dundee United | – | East Fife | | 4:0 |
| |
Scottish League Cup 1980, First Round |
| 13.08.1980 | | East Fife | – | Dundee United | | 2:5 |
| |
Scottish League Cup 1979, Second Round |
| 01.09.1979 | | East Fife | – | Raith Rovers | | 0:2 |
| |
Scottish League Cup 1979, Second Round |
| 29.08.1979 | | Raith Rovers | – | East Fife | | 1:0 |
| |
Scottish League Cup 1978/79, Second Round |
| 02.09.1978 | | Arbroath | – | East Fife | | 1:0 |
| |
Scottish League Cup 1978/79, Second Round |
| 30.08.1978 | | East Fife | – | Arbroath | | 0:1 |
| |
Scottish League Cup 1977/78, First Round |
| 24.08.1977 | | East Fife | – | Clydebank | | 0:1 |
| |
Scottish League Cup 1977/78, First Round |
| 17.08.1977 | | Clydebank | – | East Fife | | 5:0 |
| |
Scottish League Cup 1976, Group 6 |
| 01.09.1976 | | Stranraer | – | East Fife | | 5:0 |
| |
Scottish League Cup 1976, Group 6 |
| 28.08.1976 | | East Fife | – | Falkirk | | 1:5 |
| |
Scottish League Cup 1976, Group 6 |
| 18.08.1976 | | Hamilton Academical | – | East Fife | | 5:0 |
| |
Scottish League Cup 1975, Group 6 |
| 16.08.1975 | | Montrose | – | East Fife | | 4:0 |
| |
Scottish League Cup 1975, Group 6 |
| 09.08.1975 | | St. Mirren | – | East Fife | | 2:1 |
| |
Scottish League Cup 1974, Group 8 |
| 24.08.1974 | | Cowdenbeath | – | East Fife | | 2:0 |
| |
Scottish League Cup 1974, Group 8 |
| 21.08.1974 | | Falkirk | – | East Fife | | 1:0 |
| |
Scottish League Cup 1974, Group 8 |
| 14.08.1974 | | East Fife | – | Falkirk | | 1:4 |
| |
Scottish League Cup 1973, Group 4 |
| 29.08.1973 | | Dundee United | – | East Fife | | 5:2 |
| |
Scottish League Cup 1973, Group 4 |
| 25.08.1973 | | East Fife | – | Aberdeen | | 0:2 |
| |
Scottish League Cup 1973, Group 4 |
| 15.08.1973 | | Motherwell | – | East Fife | | 5:0 |
| |
Scottish League Cup 1973, Group 4 |
| 11.08.1973 | | East Fife | – | Dundee United | | 1:2 |
| |
Scottish League Cup 1972, Quarterfinal |
| 01.11.1972 | | East Fife | – | Aberdeen | | 1:4 |
| |
Scottish League Cup 1972, Quarterfinal |
| 11.10.1972 | | Aberdeen | – | East Fife | | 3:0 |
| |
Scottish League Cup 1972, Group 8 |
| 26.08.1972 | | Arbroath | – | East Fife | | 3:0 |
| |
Scottish League Cup 1972, Group 8 |
| 23.08.1972 | | East Fife | – | Celtic | | 2:3 |
| |
Scottish League Cup 1971, Group 7 |
| 01.09.1971 | | East Fife | – | Arbroath | | 0:2 |
| |
Scottish League Cup 1971, Group 7 |
| 18.08.1971 | | East Fife | – | Partick Thistle | | 2:3 |
| |
Scottish League Cup 1971, Group 7 |
| 14.08.1971 | | Raith Rovers | – | East Fife | | 2:1 |
| |
Scottish League Cup 1970, Group 5 |
| 19.08.1970 | | Stirling Albion | – | East Fife | | 2:1 |
| |
Scottish League Cup 1969, Group 5 |
| 19.08.1969 | | Albion Rovers | – | East Fife | | 2:1 |
| |
Scottish League Cup 1969, Group 5 |
| 09.08.1969 | | Motherwell | – | East Fife | | 2:0 |
| |
Scottish League Cup 1968/69, Quarterfinal |
| 25.09.1968 | | Hibernian | – | East Fife | | 2:1 |
| |
Scottish League Cup 1968/69, Quarterfinal |
| 11.09.1968 | | East Fife | – | Hibernian | | 1:4 |
| |
Scottish League Cup 1967, Quarterfinal |
| 19.09.1967 | | Dundee | – | East Fife | | 4:0 |
| |
Scottish League Cup 1967, Quarterfinal |
| 13.09.1967 | | East Fife | – | Dundee | | 0:1 |
| |
Scottish League Cup 1967, Group 8 |
| 19.08.1967 | | Arbroath | – | East Fife | | 4:3 |
| |
Scottish League Cup 1966, Group 6 |
| 31.08.1966 | | Arbroath | – | East Fife | | 2:1 |
| |
Scottish League Cup 1966, Group 6 |
| 27.08.1966 | | East Fife | – | Morton | | 0:1 |
| |
Scottish League Cup 1966, Group 6 |
| 13.08.1966 | | Morton | – | East Fife | | 2:1 |
| |
Scottish League Cup 1965, Group 8 |
| 04.09.1965 | | East Stirlingshire Clydebank | – | East Fife | | 6:2 |
| |
Scottish League Cup 1965, Group 8 |
| 01.09.1965 | | Dumbarton | – | East Fife | | 6:1 |
| |
Scottish League Cup 1965, Group 8 |
| 28.08.1965 | | East Fife | – | Alloa Athletic | | 1:2 |
| |
Scottish League Cup 1965, Group 8 |
| 14.08.1965 | | Alloa Athletic | – | East Fife | | 3:2 |
| |
Scottish League Cup 1964, Quarterfinal |
| 16.09.1964 | | Celtic | – | East Fife | | 6:0 |
| |
Scottish League Cup 1964, Supplementary Round |
| 31.08.1964 | | Forfar Athletic | – | East Fife | | 4:3 |
| |
Scottish League Cup 1964, Group 5 |
| 22.08.1964 | | East Fife | – | Raith Rovers | | 1:5 |
| |
Scottish League Cup 1963, Quarterfinal |
| 18.09.1963 | | Rangers | – | East Fife | | 2:0 |
| |
Scottish League Cup 1962, Group 7 |
| 18.08.1962 | | Queen's Park | – | East Fife | | 3:0 |
| |
Scottish League Cup 1962, Group 7 |
| 15.08.1962 | | East Fife | – | Montrose | | 0:5 |
| |
Scottish League Cup 1962, Group 7 |
| 11.08.1962 | | Queen of the South | – | East Fife | | 3:1 |
| |
Scottish League Cup 1961, Quarterfinal |
| 20.09.1961 | | East Fife | – | Rangers | | 1:3 |
| |
Scottish League Cup 1961, Quarterfinal |
| 13.09.1961 | | Rangers | – | East Fife | | 3:1 |
| |
Scottish League Cup 1960, Group 9 |
| 27.08.1960 | | East Stirlingshire | – | East Fife | | 4:1 |
| |
Scottish League Cup 1960, Group 9 |
| 13.08.1960 | | East Fife | – | Cowdenbeath | | 2:5 |
| |
Scottish League Cup 1959, Quarterfinal |
| 16.09.1959 | | East Fife | – | Cowdenbeath | | 1:2 |
| |
Scottish League Cup 1959, Quarterfinal |
| 09.09.1959 | | Cowdenbeath | – | East Fife | | 3:1 |
| |
Scottish League Cup 1958, Group 5 |
| 23.08.1958 | | Dunfermline Athletic | – | East Fife | | 5:2 |
| |
Scottish League Cup 1958, Group 5 |
| 16.08.1958 | | Stirling Albion | – | East Fife | | 1:0 |
| |
Scottish League Cup 1958, Group 5 |
| 09.08.1958 | | East Fife | – | Dunfermline Athletic | | 1:3 |
| |
Scottish League Cup 1957, Group 3 |
| 31.08.1957 | | Airdrieonians | – | East Fife | | 9:1 |
| |
Scottish League Cup 1957, Group 3 |
| 28.08.1957 | | Celtic | – | East Fife | | 6:1 |
| |
Scottish League Cup 1957, Group 3 |
| 17.08.1957 | | East Fife | – | Airdrieonians | | 1:3 |
| |
Scottish League Cup 1957, Group 3 |
| 14.08.1957 | | East Fife | – | Celtic | | 1:4 |
| |
Scottish League Cup 1957, Group 3 |
| 10.08.1957 | | Hibernian | – | East Fife | | 4:0 |
| |
Scottish League Cup 1956, Group 2 |
| 01.09.1956 | | East Fife | – | Celtic | | 0:1 |
| |
Scottish League Cup 1956, Group 2 |
| 29.08.1956 | | Aberdeen | – | East Fife | | 4:1 |
| |
Scottish League Cup 1956, Group 2 |
| 25.08.1956 | | East Fife | – | Rangers | | 1:4 |
| |
Scottish League Cup 1956, Group 2 |
| 18.08.1956 | | Celtic | – | East Fife | | 2:1 |
| |
Scottish League Cup 1956, Group 2 |
| 11.08.1956 | | Rangers | – | East Fife | | 3:0 |
| |
Scottish League Cup 1955, Group 2 |
| 03.09.1955 | | Hearts | – | East Fife | | 4:0 |
| |
Scottish League Cup 1955, Group 2 |
| 31.08.1955 | | Partick Thistle | – | East Fife | | 2:1 |
| |
Scottish League Cup 1955, Group 2 |
| 27.08.1955 | | East Fife | – | Raith Rovers | | 0:2 |
| |
Scottish League Cup 1955, Group 2 |
| 17.08.1955 | | East Fife | – | Partick Thistle | | 2:3 |
| |
Scottish League Cup 1954, Semifinal |
| 09.10.1954 | | Motherwell | – | East Fife | | 2:1 |
| |
Scottish League Cup 1954, Group 2 |
| 04.09.1954 | | Aberdeen | – | East Fife | | 5:1 |
| |
Scottish League Cup 1954, Group 2 |
| 21.08.1954 | | East Fife | – | Aberdeen | | 0:3 |
| |
Scottish League Cup 1953, Group 2 |
| 08.08.1953 | | Airdrieonians | – | East Fife | | 4:1 |
| |
Scottish League Cup 1952, Group 2 |
| 30.08.1952 | | Third Lanark | – | East Fife | | 2:0 |
| |
Scottish League Cup 1952, Group 2 |
| 16.08.1952 | | East Fife | – | Third Lanark | | 0:1 |
| |
Scottish League Cup 1951, Group 4 |
| 25.08.1951 | | Rangers | – | East Fife | | 4:1 |
| |
Scottish League Cup 1951, Group 4 |
| 15.08.1951 | | Queen of the South | – | East Fife | | 3:2 |
| |
Scottish League Cup 1950, Group 1 |
| 19.08.1950 | | East Fife | – | Third Lanark | | 2:5 |
| |
Scottish League Cup 1950, Group 1 |
| 12.08.1950 | | Celtic | – | East Fife | | 2:0 |
| |
Scottish League Cup 1948, Quarterfinal |
| 30.10.1948 | | Raith Rovers | – | East Fife | | 5:3 |
| |
Scottish League Cup 1948, Group 3 |
| 09.10.1948 | | Hearts | – | East Fife | | 6:1 |
| |
Scottish League Cup 1947, Group 8 |
| 06.09.1947 | | East Fife | – | Kilmarnock | | 1:3 |
| |
Scottish League Cup 1946/47, Quarterfinal |
| 05.03.1947 | | East Fife | – | Hearts | | 2:5 (1:3) |
| Methil |
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