Scottish League Cup 2021/22, Group D |
 | 17.07.2021 |  | Cowdenbeath | – | Brechin City | | 3:2 (2:0) |
| Cowdenbeath |
Scottish League Cup 2021/22, Group D |
| 13.07.2021 | | Alloa Athletic | – | Cowdenbeath | | 0:1 (0:0) |
| Alloa |
Scottish League Cup 2019/20, Group A |
| 13.07.2019 | | Cowdenbeath | – | East Fife | | 2:0 (2:0) |
| Cowdenbeath |
Scottish League Cup 2018/19, Group C |
| 21.07.2018 | | Cowdenbeath | – | Cove Rangers | | 1:0 (0:0) |
| Cowdenbeath |
Scottish League Cup 2018/19, Group C |
| 14.07.2018 | | Raith Rovers | – | Cowdenbeath | | 0:2 (0:0) |
| Methil |
Scottish League Cup 2017/18, Group C |
| 15.07.2017 | | Cowdenbeath | – | Buckie Thistle | | 4:2 (2:1) |
| Cowdenbeath |
Scottish League Cup 2016/17, First Round, Group C |
| 27.07.2016 | | Arbroath | – | Cowdenbeath | | 0:2 (0:2) |
| Arbroath |
Scottish League Cup 2014/15, First Round |
| 02.08.2014 | | Clyde | – | Cowdenbeath | | 1:2 (1:0) |
| Cumbernauld |
Scottish League Cup 2013/14, First Round |
| 03.08.2013 | | Berwick Rangers | – | Cowdenbeath | | 0:5 (0:2) |
| Berwick-upon-Tweed |
Scottish League Cup 2008/09, First Round |
| 05.08.2008 | | Montrose | – | Cowdenbeath | | 0:2 (0:1) |
| Montrose |
Scottish League Cup 2007/08, First Round |
| 07.08.2007 | | Cowdenbeath | – | Dumbarton | | 2:0 (0:0) |
| Cowdenbeath |
Scottish League Cup 2006/07, First Round |
| 08.08.2006 | | Cowdenbeath | – | East Stirlingshire | | 4:1 (4:0) |
| Cowdenbeath |
Scottish League Cup 2003/04, First Round |
| 02.09.2003 | | Cowdenbeath | – | Alloa Athletic | | 3:0 (0:0) |
| |
Scottish League Cup 2002/03, First Round |
| 10.09.2002 | | Cowdenbeath | – | Montrose | | 3:2 (0:0) |
| |
Scottish League Cup 2000/01, First Round |
| 08.08.2000 | | Cowdenbeath | – | Elgin City | | 3:0 |
| |
Scottish League Cup 1995, First Round |
| 05.08.1995 | | Albion Rovers | – | Cowdenbeath | | 0:1 |
| |
Scottish League Cup 1991, First Round |
| 21.08.1991 | | Cowdenbeath | – | Arbroath | | 1:0 |
| |
Scottish League Cup 1990, First Round |
| 14.08.1990 | | Stenhousemuir | – | Cowdenbeath | | 0:2 |
| |
Scottish League Cup 1985, First Round |
| 14.08.1985 | | Berwick Rangers | – | Cowdenbeath | | 1:3 |
| |
Scottish League Cup 1984, Third Round |
| 29.08.1984 | | Cowdenbeath | – | St. Mirren | | 2:0 |
| |
Scottish League Cup 1984, Second Round |
| 21.08.1984 | | Cowdenbeath | – | Partick Thistle | | 3:0 |
| |
Scottish League Cup 1984, First Round |
| 15.08.1984 | | Stranraer | – | Cowdenbeath | | 0:3 |
| |
Scottish League Cup 1983/84, Second Round |
| 24.08.1983 | | Cowdenbeath | – | Hearts | | 1:0 |
| |
Scottish League Cup 1983/84, First Round |
| 17.08.1983 | | Cowdenbeath | – | Stirling Albion | | 2:0 |
| |
Scottish League Cup 1982, Supplementary Round |
| 08.09.1982 | | Cowdenbeath | – | Kilmarnock | | 1:0 aet,
pen. 3:4 |
| |
Scottish League Cup 1982, Group 9 |
| 01.09.1982 | | Cowdenbeath | – | Meadowbank Thistle | | 3:0 |
| |
Scottish League Cup 1982, Group 9 |
| 25.08.1982 | | Cowdenbeath | – | Albion Rovers | | 2:1 |
| |
Scottish League Cup 1982, Group 9 |
| 21.08.1982 | | Meadowbank Thistle | – | Cowdenbeath | | 0:1 |
| |
Scottish League Cup 1982, Group 9 |
| 18.08.1982 | | Stranraer | – | Cowdenbeath | | 1:3 |
| |
Scottish League Cup 1981, Group 5 |
| 19.08.1981 | | Cowdenbeath | – | Brechin City | | 4:0 |
| |
Scottish League Cup 1981, Group 5 |
| 08.08.1981 | | Cowdenbeath | – | Dumbarton | | 2:0 |
| |
Scottish League Cup 1978/79, Second Round |
| 30.08.1978 | | Cowdenbeath | – | Hamilton Academical | | 3:2 |
| |
Scottish League Cup 1976, Group 7 |
| 14.08.1976 | | Cowdenbeath | – | East Stirlingshire | | 2:1 |
| |
Scottish League Cup 1975, Group 9 |
| 27.08.1975 | | Cowdenbeath | – | Forfar Athletic | | 6:2 |
| |
Scottish League Cup 1975, Group 9 |
| 23.08.1975 | | Queen's Park | – | Cowdenbeath | | 0:1 |
| |
Scottish League Cup 1975, Group 9 |
| 13.08.1975 | | Cowdenbeath | – | Brechin City | | 5:2 |
| |
Scottish League Cup 1975, Group 9 |
| 09.08.1975 | | Alloa Athletic | – | Cowdenbeath | | 1:3 |
| |
Scottish League Cup 1974, Group 8 |
| 24.08.1974 | | Cowdenbeath | – | East Fife | | 2:0 |
| |
Scottish League Cup 1973, Group 6 |
| 22.08.1973 | | Cowdenbeath | – | Raith Rovers | | 1:0 |
| |
Scottish League Cup 1972, Group 1 |
| 19.08.1972 | | Cowdenbeath | – | Morton | | 1:0 |
| |
Scottish League Cup 1971, Group 5 |
| 25.08.1971 | | Berwick Rangers | – | Cowdenbeath | | 0:1 |
| |
Scottish League Cup 1970, Quarterfinal |
| 09.09.1970 | | Falkirk | – | Cowdenbeath | | 0:1 |
| |
Scottish League Cup 1970, Group 7 |
| 26.08.1970 | | Raith Rovers | – | Cowdenbeath | | 0:2 |
| |
Scottish League Cup 1970, Group 7 |
| 22.08.1970 | | East Stirlingshire | – | Cowdenbeath | | 1:4 |
| |
Scottish League Cup 1970, Group 7 |
| 19.08.1970 | | Cowdenbeath | – | Montrose | | 3:0 |
| |
Scottish League Cup 1970, Group 7 |
| 15.08.1970 | | Cowdenbeath | – | Raith Rovers | | 3:1 |
| |
Scottish League Cup 1969, Group 7 |
| 27.08.1969 | | Cowdenbeath | – | Clydebank | | 2:1 |
| |
Scottish League Cup 1969, Group 7 |
| 13.08.1969 | | Dumbarton | – | Cowdenbeath | | 2:3 |
| |
Scottish League Cup 1967, Group 6 |
| 19.08.1967 | | Cowdenbeath | – | Montrose | | 3:0 |
| |
Scottish League Cup 1967, Group 6 |
| 16.08.1967 | | Hamilton Academical | – | Cowdenbeath | | 0:1 |
| |
Scottish League Cup 1966, Group 5 |
| 27.08.1966 | | Cowdenbeath | – | Raith Rovers | | 2:1 |
| |
Scottish League Cup 1966, Group 5 |
| 13.08.1966 | | Raith Rovers | – | Cowdenbeath | | 1:2 |
| |
Scottish League Cup 1965, Group 5 |
| 04.09.1965 | | Cowdenbeath | – | Berwick Rangers | | 3:2 |
| |
Scottish League Cup 1965, Group 5 |
| 28.08.1965 | | Hamilton Academical | – | Cowdenbeath | | 0:1 |
| |
Scottish League Cup 1963, Group 5 |
| 28.08.1963 | | Cowdenbeath | – | Alloa Athletic | | 1:0 |
| |
Scottish League Cup 1963, Group 5 |
| 14.08.1963 | | Alloa Athletic | – | Cowdenbeath | | 1:2 |
| |
Scottish League Cup 1962, Group 6 |
| 29.08.1962 | | Cowdenbeath | – | Stranraer | | 3:0 |
| |
Scottish League Cup 1961, Group 8 |
| 19.08.1961 | | Cowdenbeath | – | Dumbarton | | 4:3 |
| |
Scottish League Cup 1960, Supplementary Round |
| 07.09.1960 | | Cowdenbeath | – | Dumbarton | | 2:1 |
| |
Scottish League Cup 1960, Group 9 |
| 20.08.1960 | | Cowdenbeath | – | East Stirlingshire | | 3:0 |
| |
Scottish League Cup 1960, Group 9 |
| 17.08.1960 | | Cowdenbeath | – | Forfar Athletic | | 3:1 |
| |
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 1959, Group 8 |
| 26.08.1959 | | Cowdenbeath | – | Morton | | 3:1 |
| |
Scottish League Cup 1959, Group 8 |
| 15.08.1959 | | Cowdenbeath | – | Alloa Athletic | | 4:3 |
| |
Scottish League Cup 1959, Group 8 |
| 12.08.1959 | | Morton | – | Cowdenbeath | | 0:2 |
| |
Scottish League Cup 1959, Group 8 |
| 08.08.1959 | | Cowdenbeath | – | St. Johnstone | | 3:1 |
| |
Scottish League Cup 1958, Group 6 |
| 30.08.1958 | | Cowdenbeath | – | St. Johnstone | | 2:1 |
| |
Scottish League Cup 1958, Group 6 |
| 27.08.1958 | | Cowdenbeath | – | Dundee United | | 6:1 |
| |
Scottish League Cup 1958, Group 6 |
| 16.08.1958 | | St. Johnstone | – | Cowdenbeath | | 1:2 |
| |
Scottish League Cup 1958, Group 6 |
| 13.08.1958 | | Dundee United | – | Cowdenbeath | | 1:3 |
| |
Scottish League Cup 1958, Group 6 |
| 09.08.1958 | | Cowdenbeath | – | Morton | | 2:1 |
| |
Scottish League Cup 1956, Group 6 |
| 01.09.1956 | | Morton | – | Cowdenbeath | | 0:1 |
| |
Scottish League Cup 1956, Group 6 |
| 29.08.1956 | | Cowdenbeath | – | Berwick Rangers | | 3:1 |
| |
Scottish League Cup 1956, Group 6 |
| 25.08.1956 | | Stranraer | – | Cowdenbeath | | 1:3 |
| |
Scottish League Cup 1956, Group 6 |
| 15.08.1956 | | Berwick Rangers | – | Cowdenbeath | | 0:3 |
| |
Scottish League Cup 1955, Group 5 |
| 20.08.1955 | | Cowdenbeath | – | Arbroath | | 5:1 |
| |
Scottish League Cup 1955, Group 5 |
| 17.08.1955 | | Cowdenbeath | – | Alloa Athletic | | 5:3 |
| |
Scottish League Cup 1954, Group 7 |
| 04.09.1954 | | Cowdenbeath | – | Queen's Park | | 5:3 |
| |
Scottish League Cup 1954, Group 7 |
| 14.08.1954 | | Cowdenbeath | – | Third Lanark | | 1:0 |
| |
Scottish League Cup 1953, Group 5 |
| 22.08.1953 | | Cowdenbeath | – | St. Johnstone | | 2:1 |
| |
Scottish League Cup 1953, Group 5 |
| 15.08.1953 | | Cowdenbeath | – | Third Lanark | | 4:2 |
| |
Scottish League Cup 1953, Group 5 |
| 12.08.1953 | | Cowdenbeath | – | Alloa Athletic | | 2:1 |
| |
Scottish League Cup 1953, Group 5 |
| 08.08.1953 | | St. Johnstone | – | Cowdenbeath | | 2:4 |
| |
Scottish League Cup 1952, Group 7 |
| 09.08.1952 | | Cowdenbeath | – | Forfar Athletic | | 2:0 |
| |
Scottish League Cup 1951, Group 5 |
| 25.08.1951 | | Cowdenbeath | – | Dundee United | | 2:0 |
| |
Scottish League Cup 1950, Group 6 |
| 30.08.1950 | | Cowdenbeath | – | Stenhousemuir | | 5:1 |
| |
Scottish League Cup 1949, Quarterfinal |
| 17.09.1949 | | Rangers | – | Cowdenbeath | | 2:3 |
| |
Scottish League Cup 1949, Group 7 |
| 03.09.1949 | | Cowdenbeath | – | Ayr United | | 2:0 |
| |
Scottish League Cup 1949, Group 7 |
| 31.08.1949 | | Cowdenbeath | – | Morton | | 2:0 |
| |
Scottish League Cup 1949, Group 7 |
| 27.08.1949 | | Alloa Athletic | – | Cowdenbeath | | 1:4 |
| |
Scottish League Cup 1949, Group 7 |
| 13.08.1949 | | Cowdenbeath | – | Alloa Athletic | | 2:0 |
| |
Scottish League Cup 1947, Group 6 |
| 13.09.1947 | | Cowdenbeath | – | Dundee United | | 1:0 |
| |
Scottish League Cup 1947, Group 6 |
| 23.08.1947 | | Dundee United | – | Cowdenbeath | | 0:2 |
| |
Scottish League Cup 1946/47, Section 7 |
| 12.10.1946 | | Cowdenbeath | – | Dundee United | | 4:1 |
| |
Scottish League Cup 1946/47, Section 7 |
| 05.10.1946 | | Dumbarton | – | Cowdenbeath | | 0:4 |
| |
Scottish League Cup 1946/47, Section 7 |
| 28.09.1946 | | Cowdenbeath | – | Arbroath | | 5:2 |
| |
