Scottish League Cup 2023/24, Group G |
 | 25.07.2023 |  | Queen of the South | – | East Fife | | 0:0,
pen. 3:5 |
| Dumfries |
Scottish League Cup 2023/24, Group G |
| 15.07.2023 | | East Fife | – | Queen's Park | | 0:0,
pen. 4:2 |
| Methil |
Scottish League Cup 2022/23, Group C |
| 12.07.2022 | | Alloa Athletic | – | East Fife | | 1:1 (1:0),
pen. 6:5 |
| Alloa |
Scottish League Cup 2019/20, Group A |
| 27.07.2019 | | East Fife | – | Hearts | | 1:1 (0:1),
pen. 7:6 |
| Methil |
Scottish League Cup 2018/19, Group B |
| 22.07.2018 | | East Fife | – | Forfar Athletic | | 1:1 (1:1),
pen. 4:5 |
| Methil |
Scottish League Cup 2018/19, Group B |
| 14.07.2018 | | St. Johnstone | – | East Fife | | 0:0,
pen. 5:4 |
| Perth |
Scottish League Cup 2017/18, Group B |
| 18.07.2017 | | East Fife | – | Dunfermline Athletic | | 0:0,
pen. 8:9 |
| Methil |
Scottish League Cup 2016/17, First Round, Group A |
| 16.07.2016 | | East Fife | – | Dundee | | 1:1 (0:1),
pen. 4:2 |
| Methil |
Scottish League Cup 2015/16, First Round |
| 01.08.2015 | | East Fife | – | Dumbarton | | 1:1 aet
(0:0, 1:1),
pen. 4:3 |
| Methil |
Scottish League Cup 2011/12, Third Round |
| 20.09.2011 | | Aberdeen | – | East Fife | | 3:3 aet
(1:1, 3:3),
pen. 3:4 |
| Aberdeen |
Scottish League Cup 1999/00, Second Round |
| 17.08.1999 | | East Fife | – | Airdrieonians | | 2:2 aet,
pen. 5:4 |
| |
Scottish League Cup 1999/00, First Round |
| 31.07.1999 | | East Fife | – | Stirling Albion | | 2:2 aet,
pen. 8:7 |
| |
Scottish League Cup 1992, First Round |
| 01.08.1992 | | Stranraer | – | East Fife | | 0:0 aet,
pen. 5:4 |
| |
Scottish League Cup 1991, First Round |
| 13.08.1991 | | East Fife | – | East Stirlingshire | | 2:2 aet,
pen. 2:4 |
| |
Scottish League Cup 1990, First Round |
| 14.08.1990 | | Queen's Park | – | East Fife | | 3:3 aet,
pen. 5:4 |
| |
Scottish League Cup 1989, First Round |
| 09.08.1989 | | East Fife | – | Queen's Park | | 2:2 |
| |
Scottish League Cup 1988, Second Round |
| 17.08.1988 | | East Fife | – | Dunfermline Athletic | | 1:1 aet,
pen. 3:4 |
| |
Scottish League Cup 1987, Second Round |
| 19.08.1987 | | Albion Rovers | – | East Fife | | 1:1 aet,
pen. 5:3 |
| |
Scottish League Cup 1986, Third Round |
| 27.08.1986 | | East Fife | – | Rangers | | 0:0 aet,
pen. 4:5 |
| |
Scottish League Cup 1983/84, First Round |
| 17.08.1983 | | East Fife | – | Arbroath | | 1:1 |
| |
Scottish League Cup 1982, Group 7 |
| 01.09.1982 | | East Stirlingshire | – | East Fife | | 0:0 |
| |
Scottish League Cup 1982, Group 7 |
| 18.08.1982 | | Partick Thistle | – | East Fife | | 0:0 |
| |
Scottish League Cup 1982, Group 7 |
| 14.08.1982 | | East Fife | – | Brechin City | | 0:0 |
| |
Scottish League Cup 1981, Group 9 |
| 19.08.1981 | | East Fife | – | Arbroath | | 1:1 |
| |
Scottish League Cup 1981, Group 9 |
| 13.08.1981 | | Albion Rovers | – | East Fife | | 1:1 |
| |
Scottish League Cup 1976, Group 6 |
| 25.08.1976 | | East Fife | – | Hamilton Academical | | 1:1 |
| |
Scottish League Cup 1975, Group 6 |
| 23.08.1975 | | East Fife | – | Montrose | | 1:1 |
| |
Scottish League Cup 1975, Group 6 |
| 13.08.1975 | | East Fife | – | Raith Rovers | | 2:2 |
| |
Scottish League Cup 1973, Group 4 |
| 18.08.1973 | | Aberdeen | – | East Fife | | 1:1 |
| |
Scottish League Cup 1972, Second Round |
| 04.10.1972 | | Partick Thistle | – | East Fife | | 0:0 |
| |
Scottish League Cup 1972, Group 8 |
| 19.08.1972 | | East Fife | – | Stirling Albion | | 0:0 |
| |
Scottish League Cup 1972, Group 8 |
| 16.08.1972 | | Celtic | – | East Fife | | 1:1 |
| |
Scottish League Cup 1971, Group 7 |
| 28.08.1971 | | East Fife | – | Raith Rovers | | 1:1 |
| |
Scottish League Cup 1971, Group 7 |
| 25.08.1971 | | Partick Thistle | – | East Fife | | 1:1 |
| |
Scottish League Cup 1971, Group 7 |
| 21.08.1971 | | Arbroath | – | East Fife | | 2:2 |
| |
Scottish League Cup 1970, Group 5 |
| 15.08.1970 | | East Fife | – | Partick Thistle | | 1:1 |
| |
Scottish League Cup 1970, Group 5 |
| 12.08.1970 | | East Fife | – | Stirling Albion | | 1:1 |
| |
Scottish League Cup 1970, Group 5 |
| 08.08.1970 | | Queen of the South | – | East Fife | | 1:1 |
| |
Scottish League Cup 1969, Group 5 |
| 23.08.1969 | | East Fife | – | Motherwell | | 0:0 |
| |
Scottish League Cup 1969, Group 5 |
| 13.08.1969 | | East Fife | – | Albion Rovers | | 1:1 |
| |
Scottish League Cup 1968/69, Group 6 |
| 28.08.1968 | | East Fife | – | Queen of the South | | 1:1 |
| |
Scottish League Cup 1968/69, Group 6 |
| 14.08.1968 | | Queen of the South | – | East Fife | | 1:1 |
| |
Scottish League Cup 1966, Group 6 |
| 20.08.1966 | | East Fife | – | Third Lanark | | 2:2 |
| |
Scottish League Cup 1966, Group 6 |
| 17.08.1966 | | East Fife | – | Arbroath | | 0:0 |
| |
Scottish League Cup 1964, Group 5 |
| 26.08.1964 | | Queen of the South | – | East Fife | | 1:1 |
| |
Scottish League Cup 1963, Quarterfinal |
| 11.09.1963 | | East Fife | – | Rangers | | 1:1 |
| |
Scottish League Cup 1963, Group 8 |
| 28.08.1963 | | Arbroath | – | East Fife | | 1:1 |
| |
Scottish League Cup 1963, Group 8 |
| 10.08.1963 | | Raith Rovers | – | East Fife | | 1:1 |
| |
Scottish League Cup 1960, Group 9 |
| 20.08.1960 | | Stranraer | – | East Fife | | 2:2 |
| |
Scottish League Cup 1959, Group 7 |
| 08.08.1959 | | Brechin City | – | East Fife | | 0:0 |
| |
Scottish League Cup 1957, Group 3 |
| 24.08.1957 | | East Fife | – | Hibernian | | 2:2 |
| |
Scottish League Cup 1954, Quarterfinal |
| 22.09.1954 | | Morton | – | East Fife | | 2:2 |
| |
Scottish League Cup 1953, Group 2 |
| 12.08.1953 | | East Fife | – | Celtic | | 1:1 |
| |
Scottish League Cup 1952, Group 2 |
| 13.08.1952 | | Falkirk | – | East Fife | | 3:3 |
| |
Scottish League Cup 1951, Group 4 |
| 11.08.1951 | | East Fife | – | Rangers | | 0:0 |
| |
Scottish League Cup 1950, Group 1 |
| 02.09.1950 | | Third Lanark | – | East Fife | | 3:3 |
| |
Scottish League Cup 1950, Group 1 |
| 26.08.1950 | | East Fife | – | Celtic | | 1:1 |
| |
Scottish League Cup 1950, Group 1 |
| 16.08.1950 | | East Fife | – | Raith Rovers | | 3:3 |
| |
Scottish League Cup 1949, Group 4 |
| 20.08.1949 | | Hearts | – | East Fife | | 1:1 |
| |
Scottish League Cup 1947, Final |
| 25.10.1947 | | Falkirk | – | East Fife | | 0:0 |
| Glasgow |
Scottish League Cup 1947, Group 8 |
| 16.08.1947 | | Kilmarnock | – | East Fife | | 0:0 |
| |
