Scottish League Cup 2023/24, Group H |
| 25.07.2023 | | Cowdenbeath | | St. Mirren | | 0:1 (0:0) |
| Cowdenbeath |
Scottish League Cup 2023/24, Group H |
| 15.07.2023 | | Forfar Athletic | | Cowdenbeath | | 1:0 (1:0) |
| Forfar |
Scottish League Cup 2022/23, Group E |
| 20.07.2022 | | Edinburgh | | Cowdenbeath | | 3:0 (2:0) |
| Edinburgh |
Scottish League Cup 2022/23, Group E |
| 16.07.2022 | | Cowdenbeath | | St. Mirren | | 0:2 (0:2) |
| Cowdenbeath |
Scottish League Cup 2022/23, Group E |
| 13.07.2022 | | Arbroath | | Cowdenbeath | | 3:0 (2:0) |
| Arbroath |
Scottish League Cup 2022/23, Group E |
| 09.07.2022 | | Cowdenbeath | | Airdrieonians | | 0:3 (0:2) |
| Cowdenbeath |
Scottish League Cup 2021/22, Group D |
| 24.07.2021 | | Livingston | | Cowdenbeath | | 3:1 (2:1) |
| Livingston |
Scottish League Cup 2021/22, Group D |
| 10.07.2021 | | Cowdenbeath | | Raith Rovers | | 0:1 (0:1) |
| Cowdenbeath |
Scottish League Cup 2020/21, Group A |
| 14.11.2020 | | Cowdenbeath | | Raith Rovers | | 0:1 (0:1) |
| Cowdenbeath |
Scottish League Cup 2020/21, Group A |
| 10.10.2020 | | Cowdenbeath | | Hearts | | 0:1 (0:0) |
| Cowdenbeath |
Scottish League Cup 2020/21, Group A |
| 06.10.2020 | | East Fife | | Cowdenbeath | | 2:0 (0:0) |
| Methil |
Scottish League Cup 2019/20, Group A |
| 27.07.2019 | | Stenhousemuir | | Cowdenbeath | | 2:0 (1:0) |
| Stenhousemuir |
Scottish League Cup 2019/20, Group A |
| 19.07.2019 | | Dundee United | | Cowdenbeath | | 3:0 (1:0) |
| Dundee |
Scottish League Cup 2019/20, Group A |
| 16.07.2019 | | Cowdenbeath | | Hearts | | 0:2 (0:2) |
| Cowdenbeath |
Scottish League Cup 2018/19, Group C |
| 24.07.2018 | | Hearts | | Cowdenbeath | | 5:0 (0:0) |
| Edinburgh |
Scottish League Cup 2018/19, Group C |
| 17.07.2018 | | Cowdenbeath | | Inverness | | 2:5 (1:3) |
| Cowdenbeath |
Scottish League Cup 2017/18, Group C |
| 29.07.2017 | | Raith Rovers | | Cowdenbeath | | 2:0 (2:0) |
| Kirkcaldy |
Scottish League Cup 2017/18, Group C |
| 26.07.2017 | | Cowdenbeath | | Dundee | | 0:3 (0:3) |
| Cowdenbeath |
Scottish League Cup 2017/18, Group C |
| 23.07.2017 | | Dundee United | | Cowdenbeath | | 4:1 (1:0) |
| Dundee |
Scottish League Cup 2016/17, First Round, Group C |
| 23.07.2016 | | Cowdenbeath | | Dunfermline Athletic | | 0:3 (0:0) |
| Cowdenbeath |
Scottish League Cup 2016/17, First Round, Group C |
| 19.07.2016 | | Dundee United | | Cowdenbeath | | 6:1 (4:1) |
| Dundee |
Scottish League Cup 2016/17, First Round, Group C |
| 16.07.2016 | | Cowdenbeath | | Inverness | | 1:2 (1:1) |
| Cowdenbeath |
Scottish League Cup 2015/16, First Round |
| 01.08.2015 | | Dunfermline Athletic | | Cowdenbeath | | 5:1 (0:0) |
| Dunfermline |
Scottish League Cup 2013/14, Second Round |
| 27.08.2013 | | Partick Thistle | | Cowdenbeath | | 3:1 aet (0:0) |
| Glasgow |
Scottish League Cup 2012/13, First Round |
| 04.08.2012 | | Montrose | | Cowdenbeath | | 2:1 (2:0) |
| Montrose |
Scottish League Cup 2010/11, First Round |
| 31.07.2010 | | Clyde | | Cowdenbeath | | 2:1 (0:0) |
| Cumbernauld |
Scottish League Cup 2009/10, First Round |
| 01.08.2009 | | Cowdenbeath | | Greenock Morton | | 1:3 (1:2) |
| Cowdenbeath |
Scottish League Cup 2008/09, Second Round |
| 26.08.2008 | | Cowdenbeath | | Dundee United | | 1:5 (0:2) |
| Cowdenbeath |
Scottish League Cup 2007/08, Second Round |
| 28.08.2007 | | Gretna | | Cowdenbeath | | 3:1 (0:1) |
| Motherwell |
Scottish League Cup 2006/07, Second Round |
| 22.08.2006 | | Cowdenbeath | | Falkirk | | 0:5 (0:1) |
| Cowdenbeath |
Scottish League Cup 2005/06, First Round |
| 09.08.2005 | | Cowdenbeath | | St. Johnstone | | 2:3 (1:2) |
| |
Scottish League Cup 2004/05, First Round |
| 10.08.2004 | | Brechin City | | Cowdenbeath | | 5:2 aet (1:1, 2:2) |
| |
Scottish League Cup 2003/04, Second Round |
| 24.09.2003 | | Dunfermline Athletic | | Cowdenbeath | | 2:0 (0:0) |
| |
Scottish League Cup 2002/03, Second Round |
| 24.09.2002 | | Cowdenbeath | | Dunfermline Athletic | | 1:2 aet (1:0, 1:1) |
| |
Scottish League Cup 2001/02, First Round |
| 12.09.2001 | | Stirling Albion | | Cowdenbeath | | 3:2 |
| |
Scottish League Cup 2000/01, Second Round |
| 22.08.2000 | | St. Johnstone | | Cowdenbeath | | 3:1 |
| |
Scottish League Cup 1999/00, First Round |
| 31.07.1999 | | Cowdenbeath | | Livingston | | 1:3 |
| |
Scottish League Cup 1998, First Round |
| 01.08.1998 | | Cowdenbeath | | Livingston | | 0:2 |
| |
Scottish League Cup 1997, First Round |
| 02.08.1997 | | Cowdenbeath | | Alloa Athletic | | 0:2 |
| |
Scottish League Cup 1996, First Round |
| 03.08.1996 | | Cowdenbeath | | Forfar Athletic | | 1:2 |
| |
Scottish League Cup 1995, Second Round |
| 19.08.1995 | | Cowdenbeath | | Dundee United | | 0:4 |
| |
Scottish League Cup 1993, Second Round |
| 10.08.1993 | | Airdrieonians | | Cowdenbeath | | 2:1 |
| |
Scottish League Cup 1992, Second Round |
| 12.08.1992 | | St. Mirren | | Cowdenbeath | | 1:0 |
| |
Scottish League Cup 1991, Second Round |
| 26.08.1991 | | Cowdenbeath | | Kilmarnock | | 0:1 |
| |
Scottish League Cup 1990, Second Round |
| 22.08.1990 | | Cowdenbeath | | Hearts | | 0:2 |
| |
Scottish League Cup 1989, First Round |
| 09.08.1989 | | Cowdenbeath | | Montrose | | 0:4 aet |
| |
Scottish League Cup 1987, First Round |
| 12.08.1987 | | Cowdenbeath | | Queen's Park | | 1:3 |
| |
Scottish League Cup 1986, First Round |
| 13.08.1986 | | Cowdenbeath | | St. Johnstone | | 0:1 |
| |
Scottish League Cup 1985, Second Round |
| 21.08.1985 | | Hibernian | | Cowdenbeath | | 6:0 |
| |
Scottish League Cup 1984, Quarterfinal |
| 05.09.1984 | | Cowdenbeath | | Rangers | | 1:3 |
| |
Scottish League Cup 1982, Supplementary Round |
| 06.09.1982 | | Kilmarnock | | Cowdenbeath | | 1:0 |
| |
Scottish League Cup 1982, Group 9 |
| 14.08.1982 | | Cowdenbeath | | Montrose | | 0:1 |
| |
Scottish League Cup 1981, Group 5 |
| 22.08.1981 | | Dumbarton | | Cowdenbeath | | 3:0 |
| |
Scottish League Cup 1981, Group 5 |
| 15.08.1981 | | Cowdenbeath | | Queen of the South | | 1:2 |
| |
Scottish League Cup 1981, Group 5 |
| 12.08.1981 | | Brechin City | | Cowdenbeath | | 2:0 |
| |
Scottish League Cup 1980, Second Round |
| 30.08.1980 | | Cowdenbeath | | Dundee United | | 1:4 |
| |
Scottish League Cup 1980, Second Round |
| 27.08.1980 | | Dundee United | | Cowdenbeath | | 4:0 |
| |
Scottish League Cup 1979, Second Round |
| 01.09.1979 | | Dundee | | Cowdenbeath | | 3:1 |
| |
Scottish League Cup 1979, Second Round |
| 29.08.1979 | | Cowdenbeath | | Dundee | | 1:4 |
| |
Scottish League Cup 1978/79, Second Round |
| 02.09.1978 | | Hamilton Academical | | Cowdenbeath | | 2:0 |
| |
Scottish League Cup 1977/78, Second Round |
| 03.09.1977 | | Cowdenbeath | | Aberdeen | | 0:5 |
| |
Scottish League Cup 1977/78, Second Round |
| 31.08.1977 | | Aberdeen | | Cowdenbeath | | 5:0 |
| |
Scottish League Cup 1976, Group 7 |
| 01.09.1976 | | East Stirlingshire | | Cowdenbeath | | 4:0 |
| |
Scottish League Cup 1976, Group 7 |
| 25.08.1976 | | Cowdenbeath | | Stirling Albion | | 0:1 |
| |
Scottish League Cup 1976, Group 7 |
| 21.08.1976 | | Morton | | Cowdenbeath | | 7:1 |
| |
Scottish League Cup 1975, Supplementary Round |
| 03.09.1975 | | Clydebank | | Cowdenbeath | | 2:0 |
| |
Scottish League Cup 1975, Supplementary Round |
| 02.09.1975 | | Cowdenbeath | | Clydebank | | 0:2 |
| |
Scottish League Cup 1975, Group 9 |
| 16.08.1975 | | Cowdenbeath | | Meadowbank Thistle | | 0:2 |
| |
Scottish League Cup 1974, Group 8 |
| 28.08.1974 | | Cowdenbeath | | Falkirk | | 1:3 |
| |
Scottish League Cup 1974, Group 8 |
| 21.08.1974 | | Alloa Athletic | | Cowdenbeath | | 1:0 |
| |
Scottish League Cup 1974, Group 8 |
| 17.08.1974 | | East Fife | | Cowdenbeath | | 2:1 |
| |
Scottish League Cup 1974, Group 8 |
| 10.08.1974 | | Falkirk | | Cowdenbeath | | 4:0 |
| |
Scottish League Cup 1973, Group 6 |
| 29.08.1973 | | Queen of the South | | Cowdenbeath | | 5:1 |
| |
Scottish League Cup 1973, Group 6 |
| 25.08.1973 | | Cowdenbeath | | Stirling Albion | | 1:5 |
| |
Scottish League Cup 1973, Group 6 |
| 18.08.1973 | | Stirling Albion | | Cowdenbeath | | 4:1 |
| |
Scottish League Cup 1973, Group 6 |
| 15.08.1973 | | Raith Rovers | | Cowdenbeath | | 5:1 |
| |
Scottish League Cup 1973, Group 6 |
| 11.08.1973 | | Cowdenbeath | | Queen of the South | | 0:1 |
| |
Scottish League Cup 1972, Group 1 |
| 30.08.1972 | | Morton | | Cowdenbeath | | 7:2 |
| |
Scottish League Cup 1972, Group 1 |
| 23.08.1972 | | Cowdenbeath | | Stranraer | | 0:2 |
| |
Scottish League Cup 1972, Group 1 |
| 16.08.1972 | | Stranraer | | Cowdenbeath | | 3:0 |
| |
Scottish League Cup 1972, Group 1 |
| 12.08.1972 | | Cowdenbeath | | Partick Thistle | | 1:5 |
| |
Scottish League Cup 1971, Group 5 |
| 01.09.1971 | | Cowdenbeath | | Clydebank | | 3:4 |
| |
Scottish League Cup 1971, Group 5 |
| 21.08.1971 | | Clydebank | | Cowdenbeath | | 2:1 |
| |
Scottish League Cup 1971, Group 5 |
| 14.08.1971 | | Queen's Park | | Cowdenbeath | | 1:0 |
| |
Scottish League Cup 1970, Semifinal |
| 14.10.1970 | | Rangers | | Cowdenbeath | | 2:0 |
| |
Scottish League Cup 1970, Group 7 |
| 12.08.1970 | | Montrose | | Cowdenbeath | | 3:2 |
| |
Scottish League Cup 1969, Group 7 |
| 20.08.1969 | | Cowdenbeath | | Dumbarton | | 2:3 |
| |
Scottish League Cup 1969, Group 7 |
| 16.08.1969 | | Clydebank | | Cowdenbeath | | 3:1 |
| |
Scottish League Cup 1968/69, Group 5 |
| 31.08.1968 | | Cowdenbeath | | Stirling Albion | | 3:6 |
| |
Scottish League Cup 1968/69, Group 5 |
| 28.08.1968 | | Arbroath | | Cowdenbeath | | 2:0 |
| |
Scottish League Cup 1968/69, Group 5 |
| 24.08.1968 | | Cowdenbeath | | Ayr United | | 0:2 |
| |
Scottish League Cup 1968/69, Group 5 |
| 17.08.1968 | | Stirling Albion | | Cowdenbeath | | 2:1 |
| |
Scottish League Cup 1968/69, Group 5 |
| 10.08.1968 | | Ayr United | | Cowdenbeath | | 3:1 |
| |
Scottish League Cup 1967, Group 6 |
| 02.09.1967 | | Montrose | | Cowdenbeath | | 2:1 |
| |
Scottish League Cup 1967, Group 6 |
| 26.08.1967 | | Queen's Park | | Cowdenbeath | | 1:0 |
| |
Scottish League Cup 1967, Group 6 |
| 12.08.1967 | | Cowdenbeath | | Queen's Park | | 0:2 |
| |
Scottish League Cup 1966, Group 5 |
| 03.09.1966 | | Cowdenbeath | | Ayr United | | 0:3 |
| |
Scottish League Cup 1965, Group 5 |
| 01.09.1965 | | Cowdenbeath | | Third Lanark | | 0:1 |
| |
Scottish League Cup 1965, Group 5 |
| 21.08.1965 | | Berwick Rangers | | Cowdenbeath | | 6:1 |
| |
Scottish League Cup 1964, Group 9 |
| 29.08.1964 | | Cowdenbeath | | Brechin City | | 2:3 |
| |
Scottish League Cup 1964, Group 9 |
| 22.08.1964 | | Stirling Albion | | Cowdenbeath | | 4:0 |
| |
Scottish League Cup 1964, Group 9 |
| 08.08.1964 | | Cowdenbeath | | Forfar Athletic | | 1:2 |
| |
Scottish League Cup 1963, Group 5 |
| 31.08.1963 | | Stirling Albion | | Cowdenbeath | | 3:2 |
| |
Scottish League Cup 1963, Group 5 |
| 24.08.1963 | | Albion Rovers | | Cowdenbeath | | 2:0 |
| |
Scottish League Cup 1963, Group 5 |
| 17.08.1963 | | Cowdenbeath | | Stirling Albion | | 1:2 |
| |
Scottish League Cup 1963, Group 5 |
| 10.08.1963 | | Cowdenbeath | | Albion Rovers | | 2:3 |
| |
Scottish League Cup 1962, Group 6 |
| 01.09.1962 | | St. Johnstone | | Cowdenbeath | | 4:1 |
| |
Scottish League Cup 1962, Group 6 |
| 25.08.1962 | | Clyde | | Cowdenbeath | | 1:0 |
| |
Scottish League Cup 1962, Group 6 |
| 18.08.1962 | | Cowdenbeath | | St. Johnstone | | 0:7 |
| |
Scottish League Cup 1962, Group 6 |
| 15.08.1962 | | Stranraer | | Cowdenbeath | | 2:1 |
| |
Scottish League Cup 1962, Group 6 |
| 11.08.1962 | | Cowdenbeath | | Clyde | | 1:2 |
| |
Scottish League Cup 1961, Group 8 |
| 02.09.1961 | | Dumbarton | | Cowdenbeath | | 2:1 |
| |
Scottish League Cup 1961, Group 8 |
| 30.08.1961 | | Ayr United | | Cowdenbeath | | 3:1 |
| |
Scottish League Cup 1961, Group 8 |
| 16.08.1961 | | Cowdenbeath | | Ayr United | | 2:3 |
| |
Scottish League Cup 1960, Supplementary Round |
| 05.09.1960 | | Dumbarton | | Cowdenbeath | | 3:0 |
| |
Scottish League Cup 1960, Group 9 |
| 03.09.1960 | | Stranraer | | Cowdenbeath | | 3:1 |
| |
Scottish League Cup 1959, Semifinal |
| 07.10.1959 | | Hearts | | Cowdenbeath | | 9:3 |
| |
Scottish League Cup 1958, Quarterfinal |
| 17.09.1958 | | Cowdenbeath | | Celtic | | 1:8 |
| |
Scottish League Cup 1958, Quarterfinal |
| 10.09.1958 | | Celtic | | Cowdenbeath | | 2:0 |
| |
Scottish League Cup 1957, Group 6 |
| 31.08.1957 | | Ayr United | | Cowdenbeath | | 3:2 |
| |
Scottish League Cup 1957, Group 6 |
| 28.08.1957 | | Brechin City | | Cowdenbeath | | 7:1 |
| |
Scottish League Cup 1957, Group 6 |
| 24.08.1957 | | Cowdenbeath | | Dunfermline Athletic | | 2:5 |
| |
Scottish League Cup 1956, Quarterfinal |
| 18.09.1956 | | Partick Thistle | | Cowdenbeath | | 2:1 |
| |
Scottish League Cup 1956, Quarterfinal |
| 12.09.1956 | | Cowdenbeath | | Partick Thistle | | 1:2 |
| |
Scottish League Cup 1956, Group 6 |
| 18.08.1956 | | Cowdenbeath | | Morton | | 0:1 |
| |
Scottish League Cup 1955, Group 5 |
| 31.08.1955 | | Alloa Athletic | | Cowdenbeath | | 5:3 |
| |
Scottish League Cup 1955, Group 5 |
| 27.08.1955 | | Cowdenbeath | | Hamilton Academical | | 1:2 |
| |
Scottish League Cup 1955, Group 5 |
| 13.08.1955 | | Hamilton Academical | | Cowdenbeath | | 6:1 |
| |
Scottish League Cup 1954, Group 7 |
| 01.09.1954 | | Cowdenbeath | | Airdrieonians | | 1:2 |
| |
Scottish League Cup 1954, Group 7 |
| 28.08.1954 | | Third Lanark | | Cowdenbeath | | 4:0 |
| |
Scottish League Cup 1954, Group 7 |
| 21.08.1954 | | Queen's Park | | Cowdenbeath | | 4:1 |
| |
Scottish League Cup 1954, Group 7 |
| 18.08.1954 | | Airdrieonians | | Cowdenbeath | | 2:1 |
| |
Scottish League Cup 1953, Group 5 |
| 29.08.1953 | | Third Lanark | | Cowdenbeath | | 7:0 |
| |
Scottish League Cup 1953, Group 5 |
| 26.08.1953 | | Alloa Athletic | | Cowdenbeath | | 3:1 |
| |
Scottish League Cup 1952, Group 7 |
| 27.08.1952 | | Cowdenbeath | | Hamilton Academical | | 0:1 |
| |
Scottish League Cup 1952, Group 7 |
| 23.08.1952 | | Forfar Athletic | | Cowdenbeath | | 3:1 |
| |
Scottish League Cup 1952, Group 7 |
| 16.08.1952 | | Cowdenbeath | | Morton | | 2:3 |
| |
Scottish League Cup 1952, Group 7 |
| 13.08.1952 | | Hamilton Academical | | Cowdenbeath | | 2:0 |
| |
Scottish League Cup 1951, Group 5 |
| 01.09.1951 | | Stenhousemuir | | Cowdenbeath | | 3:1 |
| |
Scottish League Cup 1951, Group 5 |
| 29.08.1951 | | Falkirk | | Cowdenbeath | | 6:1 |
| |
Scottish League Cup 1951, Group 5 |
| 18.08.1951 | | Cowdenbeath | | Stenhousemuir | | 2:3 |
| |
Scottish League Cup 1951, Group 5 |
| 15.08.1951 | | Cowdenbeath | | Falkirk | | 0:5 |
| |
Scottish League Cup 1950, Group 6 |
| 02.09.1950 | | Dundee United | | Cowdenbeath | | 4:1 |
| |
Scottish League Cup 1950, Group 6 |
| 12.08.1950 | | Cowdenbeath | | St. Johnstone | | 0:2 |
| |
Scottish League Cup 1949, Quarterfinal |
| 21.09.1949 | | Cowdenbeath | | Rangers | | 1:3 aet |
| |
Scottish League Cup 1949, Group 7 |
| 17.08.1949 | | Morton | | Cowdenbeath | | 1:0 |
| |
Scottish League Cup 1948, Group 5 |
| 16.10.1948 | | Stirling Albion | | Cowdenbeath | | 5:2 |
| |
Scottish League Cup 1948, Group 5 |
| 09.10.1948 | | Dunfermline Athletic | | Cowdenbeath | | 3:2 |
| |
Scottish League Cup 1948, Group 5 |
| 02.10.1948 | | Cowdenbeath | | Raith Rovers | | 0:6 |
| |
Scottish League Cup 1948, Group 5 |
| 18.09.1948 | | Cowdenbeath | | Dunfermline Athletic | | 0:2 |
| |
Scottish League Cup 1947, Group 6 |
| 06.09.1947 | | Albion Rovers | | Cowdenbeath | | 4:1 |
| |
Scottish League Cup 1947, Group 6 |
| 30.08.1947 | | Cowdenbeath | | Leith Athletic | | 0:1 |
| |
Scottish League Cup 1947, Group 6 |
| 16.08.1947 | | Cowdenbeath | | Albion Rovers | | 2:3 |
| |
Scottish League Cup 1947, Group 6 |
| 09.08.1947 | | Leith Athletic | | Cowdenbeath | | 2:1 |
| |
Scottish League Cup 1946/47, Section 7 |
| 26.10.1946 | | Cowdenbeath | | Dumbarton | | 2:3 |
| |
Scottish League Cup 1946/47, Section 7 |
| 21.09.1946 | | Dundee United | | Cowdenbeath | | 2:0 |
| |