Scottish League Cup 2023/24, Group F |
 | 15.07.2023 | | Raith Rovers | – | Dunfermline Athletic | | 1:1 (1:1),
pen. 2:4 |
| Kirkcaldy |
Scottish League Cup 2022/23, Group C |
| 23.07.2022 | | Dunfermline Athletic | – | Alloa Athletic | | 1:1 (1:0),
pen. 4:5 |
| Dunfermline |
Scottish League Cup 2020/21, Quarterfinal |
| 15.12.2020 | | Dunfermline Athletic | – | St. Johnstone | | 1:1 aet
(0:0, 0:0),
pen. 3:4 |
| Dunfermline |
Scottish League Cup 2017/18, Group B |
| 29.07.2017 | | Hearts | – | Dunfermline Athletic | | 2:2 (1:1),
pen. 1:3 |
| Edinburgh |
Scottish League Cup 2017/18, Group B |
| 18.07.2017 | | East Fife | – | Dunfermline Athletic | | 0:0,
pen. 8:9 |
| Methil |
Scottish League Cup 2006/07, Second Round |
| 22.08.2006 | | Ayr United | – | Dunfermline Athletic | | 0:0 aet,
pen. 6:7 |
| Ayr |
Scottish League Cup 2001/02, Third Round |
| 09.10.2001 | | Dunfermline Athletic | – | Inverness | | 1:1 aet,
pen. 4:1 |
| |
Scottish League Cup 1997, Second Round |
| 09.08.1997 | | Dunfermline Athletic | – | Ayr United | | 0:0 aet,
pen. ?:? |
| |
Scottish League Cup 1991, Semifinal |
| 24.09.1991 | | Dunfermline Athletic | – | Airdrieonians | | 1:1 aet,
pen. 2:3 |
| Edinburgh |
Scottish League Cup 1991, Third Round |
| 28.08.1991 | | Dunfermline Athletic | – | St. Mirren | | 1:1 aet,
pen. 3:2 |
| |
Scottish League Cup 1988, Second Round |
| 17.08.1988 | | East Fife | – | Dunfermline Athletic | | 1:1 aet,
pen. 3:4 |
| |
Scottish League Cup 1985, Second Round |
| 21.08.1985 | | Morton | – | Dunfermline Athletic | | 2:2 aet,
pen. 4:3 |
| |
Scottish League Cup 1982, Group 1 |
| 18.08.1982 | | Dunfermline Athletic | – | Arbroath | | 0:0 |
| |
Scottish League Cup 1980, Second Round |
| 27.08.1980 | | Kilmarnock | – | Dunfermline Athletic | | 0:0 |
| |
Scottish League Cup 1979, First Round |
| 15.08.1979 | | Stranraer | – | Dunfermline Athletic | | 0:0 |
| |
Scottish League Cup 1977/78, Third Round |
| 26.10.1977 | | Clydebank | – | Dunfermline Athletic | | 2:2 |
| |
Scottish League Cup 1977/78, Second Round |
| 29.08.1977 | | Clyde | – | Dunfermline Athletic | | 0:0 |
| |
Scottish League Cup 1976, Group 8 |
| 01.09.1976 | | Dunfermline Athletic | – | Queen of the South | | 0:0 |
| |
Scottish League Cup 1975, Group 2 |
| 27.08.1975 | | Ayr United | – | Dunfermline Athletic | | 2:2 |
| |
Scottish League Cup 1975, Group 2 |
| 20.08.1975 | | Dunfermline Athletic | – | Dundee | | 1:1 |
| |
Scottish League Cup 1975, Group 2 |
| 09.08.1975 | | Dunfermline Athletic | – | Ayr United | | 1:1 |
| |
Scottish League Cup 1974, Group 3 |
| 28.08.1974 | | Morton | – | Dunfermline Athletic | | 1:1 |
| |
Scottish League Cup 1974, Group 3 |
| 17.08.1974 | | Dunfermline Athletic | – | Aberdeen | | 1:1 |
| |
Scottish League Cup 1974, Group 3 |
| 10.08.1974 | | Dunfermline Athletic | – | Morton | | 1:1 |
| |
Scottish League Cup 1973, Second Round |
| 10.10.1973 | | Dundee | – | Dunfermline Athletic | | 2:2 |
| |
Scottish League Cup 1973, Group 8 |
| 29.08.1973 | | Dunfermline Athletic | – | Stenhousemuir | | 2:2 |
| |
Scottish League Cup 1972, Group 4 |
| 16.08.1972 | | Dunfermline Athletic | – | Stenhousemuir | | 2:2 |
| |
Scottish League Cup 1971, Group 3 |
| 18.08.1971 | | St. Johnstone | – | Dunfermline Athletic | | 1:1 |
| |
Scottish League Cup 1970, Group 2 |
| 26.08.1970 | | Dunfermline Athletic | – | Motherwell | | 1:1 |
| |
Scottish League Cup 1969, Group 2 |
| 27.08.1969 | | Clyde | – | Dunfermline Athletic | | 0:0 |
| |
Scottish League Cup 1969, Group 2 |
| 16.08.1969 | | Dunfermline Athletic | – | Clyde | | 0:0 |
| |
Scottish League Cup 1969, Group 2 |
| 09.08.1969 | | Aberdeen | – | Dunfermline Athletic | | 2:2 |
| |
Scottish League Cup 1967, Group 1 |
| 16.08.1967 | | Dunfermline Athletic | – | Partick Thistle | | 1:1 |
| |
Scottish League Cup 1967, Group 1 |
| 12.08.1967 | | Kilmarnock | – | Dunfermline Athletic | | 2:2 |
| |
Scottish League Cup 1966, Group 3 |
| 20.08.1966 | | Dunfermline Athletic | – | Falkirk | | 2:2 |
| |
Scottish League Cup 1965, Group 3 |
| 14.08.1965 | | Partick Thistle | – | Dunfermline Athletic | | 0:0 |
| |
Scottish League Cup 1964, Quarterfinal |
| 16.09.1964 | | Rangers | – | Dunfermline Athletic | | 2:2 |
| |
Scottish League Cup 1964, Group 2 |
| 26.08.1964 | | Hibernian | – | Dunfermline Athletic | | 1:1 |
| |
Scottish League Cup 1962, Group 1 |
| 25.08.1962 | | Dunfermline Athletic | – | Raith Rovers | | 1:1 |
| |
Scottish League Cup 1962, Group 1 |
| 15.08.1962 | | Dunfermline Athletic | – | Kilmarnock | | 3:3 |
| |
Scottish League Cup 1962, Group 1 |
| 11.08.1962 | | Raith Rovers | – | Dunfermline Athletic | | 2:2 |
| |
Scottish League Cup 1961, Group 2 |
| 26.08.1961 | | Aberdeen | – | Dunfermline Athletic | | 0:0 |
| |
Scottish League Cup 1961, Group 2 |
| 19.08.1961 | | Motherwell | – | Dunfermline Athletic | | 1:1 |
| |
Scottish League Cup 1961, Group 2 |
| 16.08.1961 | | Dundee United | – | Dunfermline Athletic | | 0:0 |
| |
Scottish League Cup 1959, Group 2 |
| 08.08.1959 | | Clyde | – | Dunfermline Athletic | | 0:0 |
| |
Scottish League Cup 1958, Quarterfinal |
| 16.09.1958 | | Dunfermline Athletic | – | Kilmarnock | | 3:3 |
| |
Scottish League Cup 1957, Group 6 |
| 10.08.1957 | | Dunfermline Athletic | – | Cowdenbeath | | 1:1 |
| |
Scottish League Cup 1956, Group 3 |
| 29.08.1956 | | Queen of the South | – | Dunfermline Athletic | | 1:1 |
| |
Scottish League Cup 1956, Group 3 |
| 11.08.1956 | | Kilmarnock | – | Dunfermline Athletic | | 0:0 |
| |
Scottish League Cup 1955, Group 3 |
| 31.08.1955 | | Dunfermline Athletic | – | Aberdeen | | 2:2 |
| |
Scottish League Cup 1954, Group 6 |
| 14.08.1954 | | Brechin City | – | Dunfermline Athletic | | 1:1 |
| |
Scottish League Cup 1952, Group 5 |
| 16.08.1952 | | Alloa Athletic | – | Dunfermline Athletic | | 2:2 |
| |
Scottish League Cup 1951, Group 6 |
| 25.08.1951 | | Alloa Athletic | – | Dunfermline Athletic | | 2:2 |
| |
Scottish League Cup 1950, Group 5 |
| 30.08.1950 | | Dumbarton | – | Dunfermline Athletic | | 1:1 |
| |
Scottish League Cup 1949, Quarterfinal |
| 20.09.1949 | | Dunfermline Athletic | – | Airdrieonians | | 0:0 |
| |
Scottish League Cup 1948, Group 5 |
| 25.09.1948 | | Cowdenbeath | – | Dunfermline Athletic | | 3:3 |
| |
Scottish League Cup 1948, Group 5 |
| 11.09.1948 | | Dunfermline Athletic | – | Stirling Albion | | 1:1 |
| |
Scottish League Cup 1947, Group 5 |
| 13.09.1947 | | Alloa Athletic | – | Dunfermline Athletic | | 1:1 |
| |
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