Scottish League Cup 2023/24, Group H |
 | 22.07.2023 |  | Cowdenbeath | – | Montrose | | 1:1 (0:0),
pen. 4:5 |
| Cowdenbeath |
Scottish League Cup 2023/24, Group H |
| 19.07.2023 | | Arbroath | – | Cowdenbeath | | 1:1 (0:0),
pen. 4:3 |
| Arbroath |
Scottish League Cup 2020/21, Group A |
| 13.10.2020 | | Inverness | – | Cowdenbeath | | 0:0,
pen. 4:2 |
| Inverness |
Scottish League Cup 2014/15, Second Round |
| 26.08.2014 | | Falkirk | – | Cowdenbeath | | 0:0 aet,
pen. 4:3 |
| Falkirk |
Scottish League Cup 2011/12, First Round |
| 30.07.2011 | | Cowdenbeath | – | Stenhousemuir | | 2:2 aet,
pen. 3:4 |
| Cowdenbeath |
Scottish League Cup 1994, First Round |
| 10.08.1994 | | Stranraer | – | Cowdenbeath | | 2:2 aet,
pen. 4:2 |
| |
Scottish League Cup 1988, First Round |
| 10.08.1988 | | Cowdenbeath | – | Albion Rovers | | 0:0 aet,
pen. 3:4 |
| |
Scottish League Cup 1983/84, Second Round |
| 27.08.1983 | | Hearts | – | Cowdenbeath | | 1:1 aet,
pen. 4:2 |
| |
Scottish League Cup 1983/84, First Round |
| 15.08.1983 | | Stirling Albion | – | Cowdenbeath | | 1:1 |
| |
Scottish League Cup 1982, Group 9 |
| 28.08.1982 | | Cowdenbeath | – | Stenhousemuir | | 1:1 |
| |
Scottish League Cup 1981, Group 5 |
| 26.08.1981 | | Queen of the South | – | Cowdenbeath | | 2:2 |
| |
Scottish League Cup 1976, Group 7 |
| 28.08.1976 | | Cowdenbeath | – | Morton | | 0:0 |
| |
Scottish League Cup 1976, Group 7 |
| 18.08.1976 | | Stirling Albion | – | Cowdenbeath | | 0:0 |
| |
Scottish League Cup 1974, Group 8 |
| 14.08.1974 | | Cowdenbeath | – | Alloa Athletic | | 0:0 |
| |
Scottish League Cup 1972, Group 1 |
| 26.08.1972 | | Partick Thistle | – | Cowdenbeath | | 2:2 |
| |
Scottish League Cup 1971, Group 5 |
| 28.08.1971 | | Cowdenbeath | – | Queen's Park | | 1:1 |
| |
Scottish League Cup 1971, Group 5 |
| 18.08.1971 | | Cowdenbeath | – | Berwick Rangers | | 2:2 |
| |
Scottish League Cup 1970, Quarterfinal |
| 23.09.1970 | | Cowdenbeath | – | Falkirk | | 0:0 |
| |
Scottish League Cup 1970, Group 7 |
| 08.08.1970 | | Cowdenbeath | – | East Stirlingshire | | 1:1 |
| |
Scottish League Cup 1969, Group 7 |
| 23.08.1969 | | Stranraer | – | Cowdenbeath | | 3:3 |
| |
Scottish League Cup 1969, Group 7 |
| 09.08.1969 | | Cowdenbeath | – | Stranraer | | 2:2 |
| |
Scottish League Cup 1968/69, Group 5 |
| 14.08.1968 | | Cowdenbeath | – | Arbroath | | 1:1 |
| |
Scottish League Cup 1967, Group 6 |
| 30.08.1967 | | Cowdenbeath | – | Hamilton Academical | | 0:0 |
| |
Scottish League Cup 1966, Group 5 |
| 31.08.1966 | | Berwick Rangers | – | Cowdenbeath | | 1:1 |
| |
Scottish League Cup 1966, Group 5 |
| 20.08.1966 | | Ayr United | – | Cowdenbeath | | 2:2 |
| |
Scottish League Cup 1966, Group 5 |
| 17.08.1966 | | Cowdenbeath | – | Berwick Rangers | | 0:0 |
| |
Scottish League Cup 1965, Group 5 |
| 18.08.1965 | | Third Lanark | – | Cowdenbeath | | 1:1 |
| |
Scottish League Cup 1965, Group 5 |
| 14.08.1965 | | Cowdenbeath | – | Hamilton Academical | | 1:1 |
| |
Scottish League Cup 1964, Group 9 |
| 12.08.1964 | | Alloa Athletic | – | Cowdenbeath | | 0:0 |
| |
Scottish League Cup 1961, Group 8 |
| 26.08.1961 | | Cowdenbeath | – | Falkirk | | 1:1 |
| |
Scottish League Cup 1961, Group 8 |
| 12.08.1961 | | Falkirk | – | Cowdenbeath | | 2:2 |
| |
Scottish League Cup 1959, Group 8 |
| 29.08.1959 | | Alloa Athletic | – | Cowdenbeath | | 1:1 |
| |
Scottish League Cup 1959, Group 8 |
| 22.08.1959 | | St. Johnstone | – | Cowdenbeath | | 3:3 |
| |
Scottish League Cup 1958, Group 6 |
| 23.08.1958 | | Morton | – | Cowdenbeath | | 0:0 |
| |
Scottish League Cup 1957, Group 6 |
| 17.08.1957 | | Cowdenbeath | – | Ayr United | | 1:1 |
| |
Scottish League Cup 1957, Group 6 |
| 14.08.1957 | | Cowdenbeath | – | Brechin City | | 1:1 |
| |
Scottish League Cup 1957, Group 6 |
| 10.08.1957 | | Dunfermline Athletic | – | Cowdenbeath | | 1:1 |
| |
Scottish League Cup 1956, Group 6 |
| 11.08.1956 | | Cowdenbeath | – | Stranraer | | 1:1 |
| |
Scottish League Cup 1955, Group 5 |
| 03.09.1955 | | Arbroath | – | Cowdenbeath | | 1:1 |
| |
Scottish League Cup 1952, Group 7 |
| 30.08.1952 | | Morton | – | Cowdenbeath | | 2:2 |
| |
Scottish League Cup 1951, Group 5 |
| 11.08.1951 | | Dundee United | – | Cowdenbeath | | 1:1 |
| |
Scottish League Cup 1950, Group 6 |
| 26.08.1950 | | St. Johnstone | – | Cowdenbeath | | 2:2 |
| |
Scottish League Cup 1950, Group 6 |
| 19.08.1950 | | Cowdenbeath | – | Dundee United | | 2:2 |
| |
Scottish League Cup 1950, Group 6 |
| 16.08.1950 | | Stenhousemuir | – | Cowdenbeath | | 2:2 |
| |
Scottish League Cup 1949, Group 7 |
| 20.08.1949 | | Ayr United | – | Cowdenbeath | | 2:2 |
| |
Scottish League Cup 1948, Group 5 |
| 25.09.1948 | | Cowdenbeath | – | Dunfermline Athletic | | 3:3 |
| |
Scottish League Cup 1948, Group 5 |
| 11.09.1948 | | Raith Rovers | – | Cowdenbeath | | 3:3 |
| |
Scottish League Cup 1946/47, Section 7 |
| 19.10.1946 | | Arbroath | – | Cowdenbeath | | 3:3 |
| |
