Scottish League Cup 2023/24, Second Round |
 | 20.08.2023 |  | Hibernian | – | Raith Rovers | | 2:1 (0:0) |
| Edinburgh |
Scottish League Cup 2022/23, Group A |
| 24.07.2022 | | Aberdeen | – | Raith Rovers | | 3:0 (2:0) |
| Aberdeen |
Scottish League Cup 2021/22, Quarterfinal |
| 23.09.2021 | | Celtic | – | Raith Rovers | | 3:0 (2:0) |
| Glasgow |
Scottish League Cup 2020/21, Group A |
| 13.10.2020 | | Hearts | – | Raith Rovers | | 3:1 (2:0) |
| Edinburgh |
Scottish League Cup 2019/20, Group D |
| 27.07.2019 | | Cove Rangers | – | Raith Rovers | | 3:0 (1:0) |
| Cove |
Scottish League Cup 2019/20, Group D |
| 20.07.2019 | | Inverness | – | Raith Rovers | | 4:1 (1:0) |
| Inverness |
Scottish League Cup 2019/20, Group D |
| 13.07.2019 | | Raith Rovers | – | Dundee | | 0:3 (0:2) |
| Kirkcaldy |
Scottish League Cup 2018/19, Group C |
| 28.07.2018 | | Cove Rangers | – | Raith Rovers | | 2:0 (1:0) |
| Cove |
Scottish League Cup 2018/19, Group C |
| 24.07.2018 | | Inverness | – | Raith Rovers | | 2:1 (0:0) |
| Inverness |
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 |
| 18.07.2017 | | Raith Rovers | – | Dundee | | 1:2 (0:0) |
| Kirkcaldy |
Scottish League Cup 2017/18, Group C |
| 15.07.2017 | | Dundee United | – | Raith Rovers | | 2:0 (0:0) |
| Dundee |
Scottish League Cup 2016/17, First Round, Group D |
| 30.07.2016 | | Raith Rovers | – | Alloa Athletic | | 0:1 (0:1) |
| Kirkcaldy |
Scottish League Cup 2015/16, Third Round |
| 23.09.2015 | | Celtic | – | Raith Rovers | | 2:0 (1:0) |
| Glasgow |
Scottish League Cup 2014/15, Second Round |
| 26.08.2014 | | Dundee | – | Raith Rovers | | 4:0 (2:0) |
| Dundee |
Scottish League Cup 2012/13, Third Round |
| 25.09.2012 | | Celtic | – | Raith Rovers | | 4:1 (2:1) |
| Glasgow |
Scottish League Cup 2011/12, Second Round |
| 23.08.2011 | | Airdrie United | – | Raith Rovers | | 2:0 (2:0) |
| Airdrie |
Scottish League Cup 2010/11, Third Round |
| 22.09.2010 | | Aberdeen | – | Raith Rovers | | 3:2 (1:2) |
| Aberdeen |
Scottish League Cup 2009/10, Second Round |
| 26.08.2009 | | Dunfermline Athletic | – | Raith Rovers | | 3:1 (1:0) |
| Dunfermline |
Scottish League Cup 2008/09, Second Round |
| 26.08.2008 | | Raith Rovers | – | Falkirk | | 1:3 (0:2) |
| Kirkcaldy |
Scottish League Cup 2007/08, Second Round |
| 29.08.2007 | | Motherwell | – | Raith Rovers | | 3:1 (1:0) |
| Motherwell |
Scottish League Cup 2006/07, First Round |
| 08.08.2006 | | Raith Rovers | – | Airdrie United | | 1:2 (1:0) |
| Kirkcaldy |
Scottish League Cup 2005/06, Second Round |
| 23.08.2005 | | Raith Rovers | – | Livingston | | 1:2 (1:0) |
| |
Scottish League Cup 2004/05, First Round |
| 10.08.2004 | | Stranraer | – | Raith Rovers | | 2:1 (0:0) |
| |
Scottish League Cup 2003/04, First Round |
| 02.09.2003 | | Arbroath | – | Raith Rovers | | 1:0 (0:0) |
| |
Scottish League Cup 2002/03, First Round |
| 10.09.2002 | | Raith Rovers | – | Alloa Athletic | | 2:3 aet
(0:1, 2:2) |
| |
Scottish League Cup 2001/02, Third Round |
| 09.10.2001 | | Raith Rovers | – | Hibernian | | 0:2 |
| |
Scottish League Cup 2000/01, Third Round |
| 05.09.2000 | | Celtic | – | Raith Rovers | | 4:0 |
| |
Scottish League Cup 1998, Third Round |
| 19.08.1998 | | Hearts | – | Raith Rovers | | 4:2 |
| |
Scottish League Cup 1997, Third Round |
| 19.08.1997 | | Raith Rovers | – | Hearts | | 1:2 |
| |
Scottish League Cup 1996, Second Round |
| 13.08.1996 | | Airdrieonians | – | Raith Rovers | | 3:2 |
| |
Scottish League Cup 1995, Third Round |
| 31.08.1995 | | Celtic | – | Raith Rovers | | 2:1 |
| |
Scottish League Cup 1993, Second Round |
| 11.08.1993 | | Raith Rovers | – | Arbroath | | 1:2 |
| |
Scottish League Cup 1992, Second Round |
| 12.08.1992 | | Hibernian | – | Raith Rovers | | 4:1 |
| |
Scottish League Cup 1991, Third Round |
| 27.08.1991 | | Celtic | – | Raith Rovers | | 3:1 |
| |
Scottish League Cup 1990, Quarterfinal |
| 04.09.1990 | | Rangers | – | Raith Rovers | | 6:2 |
| Glasgow |
Scottish League Cup 1989, Second Round |
| 15.08.1989 | | Dunfermline Athletic | – | Raith Rovers | | 3:0 |
| |
Scottish League Cup 1987, Third Round |
| 25.08.1987 | | Raith Rovers | – | Dundee United | | 1:2 |
| |
Scottish League Cup 1986, First Round |
| 13.08.1986 | | Arbroath | – | Raith Rovers | | 2:1 |
| |
Scottish League Cup 1985, Second Round |
| 21.08.1985 | | Clydebank | – | Raith Rovers | | 7:2 |
| |
Scottish League Cup 1984, Third Round |
| 29.08.1984 | | Rangers | – | Raith Rovers | | 4:0 |
| |
Scottish League Cup 1983/84, Second Round |
| 27.08.1983 | | Raith Rovers | – | Aberdeen | | 0:3 |
| |
Scottish League Cup 1983/84, Second Round |
| 24.08.1983 | | Aberdeen | – | Raith Rovers | | 9:0 |
| |
Scottish League Cup 1982, Group 4 |
| 01.09.1982 | | Raith Rovers | – | Dundee United | | 1:3 |
| |
Scottish League Cup 1982, Group 4 |
| 28.08.1982 | | Falkirk | – | Raith Rovers | | 2:0 |
| |
Scottish League Cup 1982, Group 4 |
| 21.08.1982 | | Dundee United | – | Raith Rovers | | 5:1 |
| |
Scottish League Cup 1982, Group 4 |
| 18.08.1982 | | St. Johnstone | – | Raith Rovers | | 5:0 |
| |
Scottish League Cup 1981, Group 2 |
| 26.08.1981 | | Raith Rovers | – | Rangers | | 1:3 |
| |
Scottish League Cup 1981, Group 2 |
| 19.08.1981 | | Morton | – | Raith Rovers | | 2:0 |
| |
Scottish League Cup 1981, Group 2 |
| 15.08.1981 | | Rangers | – | Raith Rovers | | 8:1 |
| |
Scottish League Cup 1981, Group 2 |
| 12.08.1981 | | Raith Rovers | – | Morton | | 2:5 |
| |
Scottish League Cup 1980, Third Round |
| 24.09.1980 | | Clydebank | – | Raith Rovers | | 1:0 |
| |
Scottish League Cup 1980, Third Round |
| 03.09.1980 | | Raith Rovers | – | Clydebank | | 0:1 |
| |
Scottish League Cup 1979, Quarterfinal |
| 14.11.1979 | | Raith Rovers | – | Dundee United | | 0:1 |
| |
Scottish League Cup 1978/79, Third Round |
| 11.10.1978 | | Montrose | – | Raith Rovers | | 5:1 |
| |
Scottish League Cup 1978/79, Second Round |
| 02.09.1978 | | Queen's Park | – | Raith Rovers | | 4:2 aet,
pen. ?:? |
| |
Scottish League Cup 1977/78, Second Round |
| 03.09.1977 | | Arbroath | – | Raith Rovers | | 3:1 |
| |
Scottish League Cup 1977/78, Second Round |
| 31.08.1977 | | Raith Rovers | – | Arbroath | | 0:1 |
| |
Scottish League Cup 1976, Group 5 |
| 25.08.1976 | | Airdrieonians | – | Raith Rovers | | 7:1 |
| |
Scottish League Cup 1976, Group 5 |
| 21.08.1976 | | Raith Rovers | – | Queen's Park | | 0:1 |
| |
Scottish League Cup 1976, Group 5 |
| 18.08.1976 | | Raith Rovers | – | Airdrieonians | | 1:4 |
| |
Scottish League Cup 1975, Group 6 |
| 27.08.1975 | | Montrose | – | Raith Rovers | | 2:1 |
| |
Scottish League Cup 1975, Group 6 |
| 20.08.1975 | | Raith Rovers | – | East Fife | | 0:2 |
| |
Scottish League Cup 1974, Group 5 |
| 28.08.1974 | | Queen of the South | – | Raith Rovers | | 2:0 |
| |
Scottish League Cup 1974, Group 5 |
| 17.08.1974 | | Hamilton Academical | – | Raith Rovers | | 1:0 |
| |
Scottish League Cup 1974, Group 5 |
| 14.08.1974 | | Berwick Rangers | – | Raith Rovers | | 2:0 |
| |
Scottish League Cup 1973, Second Round |
| 10.10.1973 | | Raith Rovers | – | Hibernian | | 0:2 |
| |
Scottish League Cup 1973, Second Round |
| 12.09.1973 | | Hibernian | – | Raith Rovers | | 3:2 |
| |
Scottish League Cup 1973, Group 6 |
| 22.08.1973 | | Cowdenbeath | – | Raith Rovers | | 1:0 |
| |
Scottish League Cup 1973, Group 6 |
| 11.08.1973 | | Stirling Albion | – | Raith Rovers | | 1:0 |
| |
Scottish League Cup 1972, Group 5 |
| 23.08.1972 | | Montrose | – | Raith Rovers | | 2:1 |
| |
Scottish League Cup 1972, Group 5 |
| 19.08.1972 | | Falkirk | – | Raith Rovers | | 1:0 |
| |
Scottish League Cup 1972, Group 5 |
| 16.08.1972 | | Raith Rovers | – | Montrose | | 1:2 |
| |
Scottish League Cup 1972, Group 5 |
| 12.08.1972 | | St. Johnstone | – | Raith Rovers | | 2:0 |
| |
Scottish League Cup 1971, Group 7 |
| 01.09.1971 | | Partick Thistle | – | Raith Rovers | | 5:0 |
| |
Scottish League Cup 1971, Group 7 |
| 18.08.1971 | | Arbroath | – | Raith Rovers | | 4:0 |
| |
Scottish League Cup 1970, Group 7 |
| 26.08.1970 | | Raith Rovers | – | Cowdenbeath | | 0:2 |
| |
Scottish League Cup 1970, Group 7 |
| 22.08.1970 | | Montrose | – | Raith Rovers | | 4:1 |
| |
Scottish League Cup 1970, Group 7 |
| 15.08.1970 | | Cowdenbeath | – | Raith Rovers | | 3:1 |
| |
Scottish League Cup 1970, Group 7 |
| 12.08.1970 | | East Stirlingshire | – | Raith Rovers | | 2:0 |
| |
Scottish League Cup 1969, Group 1 |
| 27.08.1969 | | Raith Rovers | – | Celtic | | 2:5 |
| |
Scottish League Cup 1969, Group 1 |
| 16.08.1969 | | Celtic | – | Raith Rovers | | 5:0 |
| |
Scottish League Cup 1969, Group 1 |
| 13.08.1969 | | Airdrieonians | – | Raith Rovers | | 3:1 |
| |
Scottish League Cup 1969, Group 1 |
| 09.08.1969 | | Raith Rovers | – | Rangers | | 2:3 |
| |
Scottish League Cup 1968/69, Group 1 |
| 28.08.1968 | | Hibernian | – | Raith Rovers | | 3:0 |
| |
Scottish League Cup 1968/69, Group 1 |
| 14.08.1968 | | Raith Rovers | – | Hibernian | | 0:1 |
| |
Scottish League Cup 1967, Group 7 |
| 02.09.1967 | | Queen of the South | – | Raith Rovers | | 3:2 |
| |
Scottish League Cup 1967, Group 7 |
| 30.08.1967 | | Raith Rovers | – | Morton | | 2:3 |
| |
Scottish League Cup 1967, Group 7 |
| 19.08.1967 | | Raith Rovers | – | Queen of the South | | 2:5 |
| |
Scottish League Cup 1967, Group 7 |
| 16.08.1967 | | Morton | – | Raith Rovers | | 3:1 |
| |
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, Quarterfinal |
| 22.09.1965 | | Celtic | – | Raith Rovers | | 4:0 |
| |
Scottish League Cup 1965, Quarterfinal |
| 15.09.1965 | | Raith Rovers | – | Celtic | | 1:8 |
| |
Scottish League Cup 1964, Group 5 |
| 29.08.1964 | | Raith Rovers | – | Queen of the South | | 2:3 |
| |
Scottish League Cup 1964, Group 5 |
| 08.08.1964 | | Raith Rovers | – | East Fife | | 1:4 |
| |
Scottish League Cup 1963, Group 8 |
| 31.08.1963 | | Arbroath | – | Raith Rovers | | 2:0 |
| |
Scottish League Cup 1963, Group 8 |
| 28.08.1963 | | Raith Rovers | – | Dumbarton | | 1:2 |
| |
Scottish League Cup 1963, Group 8 |
| 24.08.1963 | | East Fife | – | Raith Rovers | | 3:0 |
| |
Scottish League Cup 1963, Group 8 |
| 17.08.1963 | | Raith Rovers | – | Arbroath | | 3:4 |
| |
Scottish League Cup 1963, Group 8 |
| 14.08.1963 | | Dumbarton | – | Raith Rovers | | 3:0 |
| |
Scottish League Cup 1962, Group 1 |
| 01.09.1962 | | Kilmarnock | – | Raith Rovers | | 3:1 |
| |
Scottish League Cup 1962, Group 1 |
| 18.08.1962 | | Raith Rovers | – | Kilmarnock | | 2:3 |
| |
Scottish League Cup 1961, Group 4 |
| 02.09.1961 | | Kilmarnock | – | Raith Rovers | | 4:1 |
| |
Scottish League Cup 1961, Group 4 |
| 19.08.1961 | | Raith Rovers | – | Kilmarnock | | 1:7 |
| |
Scottish League Cup 1961, Group 4 |
| 16.08.1961 | | Raith Rovers | – | St. Mirren | | 0:3 |
| |
Scottish League Cup 1961, Group 4 |
| 12.08.1961 | | Hearts | – | Raith Rovers | | 1:0 |
| |
Scottish League Cup 1960, Group 4 |
| 31.08.1960 | | Aberdeen | – | Raith Rovers | | 3:0 |
| |
Scottish League Cup 1960, Group 4 |
| 27.08.1960 | | Raith Rovers | – | Dundee | | 0:3 |
| |
Scottish League Cup 1960, Group 4 |
| 13.08.1960 | | Dundee | – | Raith Rovers | | 5:0 |
| |
Scottish League Cup 1959, Quarterfinal |
| 16.09.1959 | | Arbroath | – | Raith Rovers | | 2:1 aet |
| |
Scottish League Cup 1959, Group 1 |
| 22.08.1959 | | Celtic | – | Raith Rovers | | 1:0 |
| |
Scottish League Cup 1958, Group 1 |
| 30.08.1958 | | Hearts | – | Raith Rovers | | 3:1 |
| |
Scottish League Cup 1958, Group 1 |
| 27.08.1958 | | Rangers | – | Raith Rovers | | 6:0 |
| |
Scottish League Cup 1958, Group 1 |
| 16.08.1958 | | Raith Rovers | – | Hearts | | 1:3 |
| |
Scottish League Cup 1958, Group 1 |
| 09.08.1958 | | Third Lanark | – | Raith Rovers | | 4:2 |
| |
Scottish League Cup 1957, Group 2 |
| 17.08.1957 | | Rangers | – | Raith Rovers | | 4:3 |
| |
Scottish League Cup 1957, Group 2 |
| 13.08.1957 | | St. Mirren | – | Raith Rovers | | 1:0 |
| |
Scottish League Cup 1956, Group 1 |
| 25.08.1956 | | Airdrieonians | – | Raith Rovers | | 3:1 |
| |
Scottish League Cup 1956, Group 1 |
| 15.08.1956 | | Dundee | – | Raith Rovers | | 1:0 |
| |
Scottish League Cup 1955, Group 2 |
| 03.09.1955 | | Raith Rovers | – | Partick Thistle | | 0:1 |
| |
Scottish League Cup 1955, Group 2 |
| 31.08.1955 | | Raith Rovers | – | Hearts | | 0:2 |
| |
Scottish League Cup 1955, Group 2 |
| 20.08.1955 | | Partick Thistle | – | Raith Rovers | | 4:0 |
| |
Scottish League Cup 1955, Group 2 |
| 17.08.1955 | | Hearts | – | Raith Rovers | | 5:0 |
| |
Scottish League Cup 1955, Group 2 |
| 13.08.1955 | | Raith Rovers | – | East Fife | | 2:4 |
| |
Scottish League Cup 1954, Group 1 |
| 01.09.1954 | | St. Mirren | – | Raith Rovers | | 3:1 |
| |
Scottish League Cup 1954, Group 1 |
| 28.08.1954 | | Raith Rovers | – | Kilmarnock | | 0:1 |
| |
Scottish League Cup 1954, Group 1 |
| 14.08.1954 | | Kilmarnock | – | Raith Rovers | | 3:2 |
| |
Scottish League Cup 1953, Group 3 |
| 22.08.1953 | | Rangers | – | Raith Rovers | | 3:1 |
| |
Scottish League Cup 1953, Group 3 |
| 15.08.1953 | | Hearts | – | Raith Rovers | | 2:0 |
| |
Scottish League Cup 1953, Group 3 |
| 08.08.1953 | | Raith Rovers | – | Rangers | | 0:4 |
| |
Scottish League Cup 1952, Group 4 |
| 27.08.1952 | | Clyde | – | Raith Rovers | | 6:1 |
| |
Scottish League Cup 1952, Group 4 |
| 23.08.1952 | | Raith Rovers | – | Dundee | | 1:2 |
| |
Scottish League Cup 1952, Group 4 |
| 09.08.1952 | | Dundee | – | Raith Rovers | | 2:1 |
| |
Scottish League Cup 1951, Group 3 |
| 01.09.1951 | | Raith Rovers | – | Dundee | | 1:3 |
| |
Scottish League Cup 1951, Group 3 |
| 29.08.1951 | | St. Mirren | – | Raith Rovers | | 2:0 |
| |
Scottish League Cup 1951, Group 3 |
| 18.08.1951 | | Dundee | – | Raith Rovers | | 5:0 |
| |
Scottish League Cup 1951, Group 3 |
| 11.08.1951 | | Hearts | – | Raith Rovers | | 1:0 |
| |
Scottish League Cup 1950, Group 1 |
| 30.08.1950 | | Raith Rovers | – | East Fife | | 1:4 |
| |
Scottish League Cup 1950, Group 1 |
| 26.08.1950 | | Third Lanark | – | Raith Rovers | | 1:0 |
| |
Scottish League Cup 1950, Group 1 |
| 19.08.1950 | | Celtic | – | Raith Rovers | | 2:1 |
| |
Scottish League Cup 1949, Group 4 |
| 03.09.1949 | | Stirling Albion | – | Raith Rovers | | 4:1 |
| |
Scottish League Cup 1949, Group 4 |
| 31.08.1949 | | Raith Rovers | – | Hearts | | 1:2 |
| |
Scottish League Cup 1949, Group 4 |
| 27.08.1949 | | East Fife | – | Raith Rovers | | 3:2 |
| |
Scottish League Cup 1949, Group 4 |
| 17.08.1949 | | Hearts | – | Raith Rovers | | 5:1 |
| |
Scottish League Cup 1949, Group 4 |
| 13.08.1949 | | Raith Rovers | – | East Fife | | 0:3 |
| |
Scottish League Cup 1948, Final |
| 12.03.1949 | | Rangers | – | Raith Rovers | | 2:0 |
| Glasgow |
Scottish League Cup 1948, Group 5 |
| 16.10.1948 | | Dunfermline Athletic | – | Raith Rovers | | 1:0 |
| |
Scottish League Cup 1947, Group 5 |
| 13.09.1947 | | Hamilton Academical | – | Raith Rovers | | 6:1 |
| |
Scottish League Cup 1946/47, Section 6 |
| 26.10.1946 | | Raith Rovers | – | Stenhousemuir | | 2:4 |
| |
Scottish League Cup 1946/47, Section 6 |
| 12.10.1946 | | Dundee | – | Raith Rovers | | 3:0 |
| |
Scottish League Cup 1946/47, Section 6 |
| 21.09.1946 | | Raith Rovers | – | Dundee | | 0:2 |
| |
