Scottish League Cup 2023/24, Group F |
 | 29.07.2023 |  | Annan Athletic | – | Raith Rovers | | 2:3 (2:1) |
| Annan |
Scottish League Cup 2023/24, Group F |
| 18.07.2023 | | Raith Rovers | – | Albion Rovers | | 2:0 (0:0) |
| Kirkcaldy |
Scottish League Cup 2022/23, Group A |
| 13.07.2022 | | Raith Rovers | – | Peterhead | | 6:0 (2:0) |
| Kirkcaldy |
Scottish League Cup 2021/22, Second round |
| 15.08.2021 | | Raith Rovers | – | Aberdeen | | 2:1 (0:1) |
| Kirkcaldy |
Scottish League Cup 2021/22, Group D |
| 13.07.2021 | | Raith Rovers | – | Brechin City | | 4:0 (1:0) |
| Kirkcaldy |
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 | | Raith Rovers | – | East Fife | | 2:1 (1:1) |
| Kirkcaldy |
Scottish League Cup 2019/20, Group D |
| 23.07.2019 | | Raith Rovers | – | Peterhead | | 3:1 (2:0) |
| Kirkcaldy |
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 |
| 25.07.2017 | | Buckie Thistle | – | Raith Rovers | | 1:6 (1:3) |
| Buckie |
Scottish League Cup 2016/17, First Round, Group D |
| 19.07.2016 | | Raith Rovers | – | Montrose | | 2:1 (1:0) |
| Kirkcaldy |
Scottish League Cup 2016/17, First Round, Group D |
| 15.07.2016 | | Cove Rangers | – | Raith Rovers | | 1:2 (1:1) |
| Forfar |
Scottish League Cup 2015/16, Second Round |
| 25.08.2015 | | Raith Rovers | – | Hamilton Academical | | 2:1 (1:0) |
| Kirkcaldy |
Scottish League Cup 2015/16, First Round |
| 01.08.2015 | | Raith Rovers | – | Albion Rovers | | 3:0 (2:0) |
| Kirkcaldy |
Scottish League Cup 2014/15, First Round |
| 02.08.2014 | | Raith Rovers | – | Forfar Athletic | | 4:2 aet
(1:1, 2:2) |
| Kirkcaldy |
Scottish League Cup 2013/14, First Round |
| 03.08.2013 | | Raith Rovers | – | Queen's Park | | 6:0 (2:0) |
| Kirkcaldy |
Scottish League Cup 2012/13, Second Round |
| 28.08.2012 | | Ross County | – | Raith Rovers | | 1:4 (0:2) |
| Dingwall |
Scottish League Cup 2012/13, First Round |
| 04.08.2012 | | Raith Rovers | – | Berwick Rangers | | 4:3 (1:1) |
| Kirkcaldy |
Scottish League Cup 2011/12, First Round |
| 30.07.2011 | | Montrose | – | Raith Rovers | | 1:4 (1:1) |
| Montrose |
Scottish League Cup 2010/11, Second Round |
| 24.08.2010 | | Raith Rovers | – | Hamilton Academical | | 1:0 (0:0) |
| Kirkcaldy |
Scottish League Cup 2010/11, First Round |
| 31.07.2010 | | Raith Rovers | – | East Fife | | 4:1 (3:0) |
| Kirkcaldy |
Scottish League Cup 2009/10, First Round |
| 01.08.2009 | | East Fife | – | Raith Rovers | | 2:3 (2:0) |
| Methil |
Scottish League Cup 2007/08, First Round |
| 07.08.2007 | | Clyde | – | Raith Rovers | | 0:3 (0:1) |
| Cumbernauld |
Scottish League Cup 2005/06, First Round |
| 09.08.2005 | | Raith Rovers | – | Airdrie United | | 2:0 (1:0) |
| |
Scottish League Cup 2001/02, Second Round |
| 25.09.2001 | | Falkirk | – | Raith Rovers | | 0:2 |
| |
Scottish League Cup 2001/02, First Round |
| 11.09.2001 | | Raith Rovers | – | Montrose | | 1:0 |
| |
Scottish League Cup 2000/01, Second Round |
| 22.08.2000 | | Raith Rovers | – | Arbroath | | 2:1 |
| |
Scottish League Cup 2000/01, First Round |
| 08.08.2000 | | East Fife | – | Raith Rovers | | 1:2 |
| |
Scottish League Cup 1999/00, First Round |
| 31.07.1999 | | Stranraer | – | Raith Rovers | | 0:1 aet
(0:0) |
| |
Scottish League Cup 1998, Second Round |
| 08.08.1998 | | Raith Rovers | – | Clydebank | | 2:0 |
| |
Scottish League Cup 1997, Second Round |
| 09.08.1997 | | Raith Rovers | – | Forfar Athletic | | 5:0 |
| |
Scottish League Cup 1995, Second Round |
| 19.08.1995 | | Raith Rovers | – | Arbroath | | 2:1 |
| |
Scottish League Cup 1994, Quarterfinal |
| 20.09.1994 | | St. Johnstone | – | Raith Rovers | | 1:3 |
| Perth |
Scottish League Cup 1994, Third Round |
| 31.08.1994 | | Raith Rovers | – | Kilmarnock | | 3:2 |
| |
Scottish League Cup 1994, Second Round |
| 17.08.1994 | | Ross County | – | Raith Rovers | | 0:5 |
| |
Scottish League Cup 1991, Second Round |
| 20.08.1991 | | Raith Rovers | – | Motherwell | | 4:1 |
| |
Scottish League Cup 1990, Third Round |
| 29.08.1990 | | Raith Rovers | – | Hibernian | | 1:0 |
| |
Scottish League Cup 1990, Second Round |
| 21.08.1990 | | Forfar Athletic | – | Raith Rovers | | 1:2 |
| |
Scottish League Cup 1987, Second Round |
| 19.08.1987 | | Raith Rovers | – | Clydebank | | 2:1 |
| |
Scottish League Cup 1985, First Round |
| 14.08.1985 | | East Stirlingshire | – | Raith Rovers | | 1:3 |
| |
Scottish League Cup 1984, Second Round |
| 21.08.1984 | | Raith Rovers | – | Clydebank | | 2:0 |
| |
Scottish League Cup 1981, Group 2 |
| 08.08.1981 | | Dundee | – | Raith Rovers | | 1:2 |
| |
Scottish League Cup 1980, Second Round |
| 27.08.1980 | | Dumbarton | – | Raith Rovers | | 0:1 |
| |
Scottish League Cup 1980, First Round |
| 20.08.1980 | | Falkirk | – | Raith Rovers | | 0:2 |
| |
Scottish League Cup 1980, First Round |
| 13.08.1980 | | Raith Rovers | – | Falkirk | | 3:2 |
| |
Scottish League Cup 1979, Third Round |
| 10.10.1979 | | St. Johnstone | – | Raith Rovers | | 1:3 |
| |
Scottish League Cup 1979, Second Round |
| 01.09.1979 | | East Fife | – | Raith Rovers | | 0:2 |
| |
Scottish League Cup 1979, Second Round |
| 29.08.1979 | | Raith Rovers | – | East Fife | | 1:0 |
| |
Scottish League Cup 1978/79, Third Round |
| 04.10.1978 | | Raith Rovers | – | Montrose | | 3:0 |
| |
Scottish League Cup 1978/79, Second Round |
| 30.08.1978 | | Raith Rovers | – | Queen's Park | | 4:2 |
| |
Scottish League Cup 1976, Group 5 |
| 28.08.1976 | | Queen's Park | – | Raith Rovers | | 0:4 |
| |
Scottish League Cup 1975, Group 6 |
| 16.08.1975 | | Raith Rovers | – | St. Mirren | | 1:0 |
| |
Scottish League Cup 1975, Group 6 |
| 09.08.1975 | | Raith Rovers | – | Montrose | | 2:1 |
| |
Scottish League Cup 1974, Group 5 |
| 24.08.1974 | | Raith Rovers | – | Hamilton Academical | | 2:1 |
| |
Scottish League Cup 1974, Group 5 |
| 21.08.1974 | | Raith Rovers | – | Berwick Rangers | | 1:0 |
| |
Scottish League Cup 1973, Group 6 |
| 29.08.1973 | | Raith Rovers | – | Stirling Albion | | 1:0 |
| |
Scottish League Cup 1973, Group 6 |
| 25.08.1973 | | Queen of the South | – | Raith Rovers | | 1:2 |
| |
Scottish League Cup 1973, Group 6 |
| 15.08.1973 | | Raith Rovers | – | Cowdenbeath | | 5:1 |
| |
Scottish League Cup 1972, Group 5 |
| 30.08.1972 | | Raith Rovers | – | Falkirk | | 1:0 |
| |
Scottish League Cup 1972, Group 5 |
| 26.08.1972 | | Raith Rovers | – | St. Johnstone | | 3:0 |
| |
Scottish League Cup 1971, Group 7 |
| 14.08.1971 | | Raith Rovers | – | East Fife | | 2:1 |
| |
Scottish League Cup 1970, Group 7 |
| 19.08.1970 | | Raith Rovers | – | East Stirlingshire | | 2:1 |
| |
Scottish League Cup 1970, Group 7 |
| 08.08.1970 | | Raith Rovers | – | Montrose | | 1:0 |
| |
Scottish League Cup 1969, Group 1 |
| 20.08.1969 | | Raith Rovers | – | Airdrieonians | | 2:1 |
| |
Scottish League Cup 1968/69, Group 1 |
| 31.08.1968 | | Raith Rovers | – | St. Johnstone | | 2:1 |
| |
Scottish League Cup 1968/69, Group 1 |
| 24.08.1968 | | Raith Rovers | – | Falkirk | | 4:2 |
| |
Scottish League Cup 1967, Group 7 |
| 12.08.1967 | | Raith Rovers | – | Dumbarton | | 2:0 |
| |
Scottish League Cup 1966, Group 5 |
| 03.09.1966 | | Raith Rovers | – | Berwick Rangers | | 2:0 |
| |
Scottish League Cup 1966, Group 5 |
| 31.08.1966 | | Raith Rovers | – | Ayr United | | 3:1 |
| |
Scottish League Cup 1965, Group 6 |
| 04.09.1965 | | Raith Rovers | – | Queen's Park | | 3:0 |
| |
Scottish League Cup 1965, Group 6 |
| 01.09.1965 | | Raith Rovers | – | Arbroath | | 4:2 |
| |
Scottish League Cup 1965, Group 6 |
| 28.08.1965 | | Stirling Albion | – | Raith Rovers | | 1:2 |
| |
Scottish League Cup 1965, Group 6 |
| 14.08.1965 | | Raith Rovers | – | Stirling Albion | | 3:1 |
| |
Scottish League Cup 1964, Group 5 |
| 26.08.1964 | | Raith Rovers | – | Montrose | | 7:0 |
| |
Scottish League Cup 1964, Group 5 |
| 22.08.1964 | | East Fife | – | Raith Rovers | | 1:5 |
| |
Scottish League Cup 1964, Group 5 |
| 12.08.1964 | | Montrose | – | Raith Rovers | | 2:4 |
| |
Scottish League Cup 1962, Group 1 |
| 29.08.1962 | | Raith Rovers | – | Airdrieonians | | 3:1 |
| |
Scottish League Cup 1961, Group 4 |
| 30.08.1961 | | St. Mirren | – | Raith Rovers | | 0:2 |
| |
Scottish League Cup 1961, Group 4 |
| 26.08.1961 | | Raith Rovers | – | Hearts | | 3:1 |
| |
Scottish League Cup 1960, Group 4 |
| 03.09.1960 | | Ayr United | – | Raith Rovers | | 1:2 |
| |
Scottish League Cup 1960, Group 4 |
| 17.08.1960 | | Raith Rovers | – | Aberdeen | | 4:1 |
| |
Scottish League Cup 1959, Group 1 |
| 29.08.1959 | | Partick Thistle | – | Raith Rovers | | 1:3 |
| |
Scottish League Cup 1959, Group 1 |
| 26.08.1959 | | Raith Rovers | – | Airdrieonians | | 3:0 |
| |
Scottish League Cup 1959, Group 1 |
| 15.08.1959 | | Raith Rovers | – | Partick Thistle | | 2:0 |
| |
Scottish League Cup 1959, Group 1 |
| 12.08.1959 | | Airdrieonians | – | Raith Rovers | | 2:3 |
| |
Scottish League Cup 1959, Group 1 |
| 08.08.1959 | | Raith Rovers | – | Celtic | | 2:1 |
| |
Scottish League Cup 1958, Group 1 |
| 23.08.1958 | | Raith Rovers | – | Third Lanark | | 3:1 |
| |
Scottish League Cup 1958, Group 1 |
| 13.08.1958 | | Raith Rovers | – | Rangers | | 3:1 |
| |
Scottish League Cup 1957, Group 2 |
| 31.08.1957 | | Raith Rovers | – | Rangers | | 4:3 |
| |
Scottish League Cup 1957, Group 2 |
| 28.08.1957 | | Raith Rovers | – | St. Mirren | | 4:1 |
| |
Scottish League Cup 1957, Group 2 |
| 24.08.1957 | | Partick Thistle | – | Raith Rovers | | 1:4 |
| |
Scottish League Cup 1957, Group 2 |
| 10.08.1957 | | Raith Rovers | – | Partick Thistle | | 1:0 |
| |
Scottish League Cup 1956, Group 1 |
| 01.09.1956 | | Motherwell | – | Raith Rovers | | 0:1 |
| |
Scottish League Cup 1956, Group 1 |
| 18.08.1956 | | Raith Rovers | – | Motherwell | | 4:2 |
| |
Scottish League Cup 1956, Group 1 |
| 11.08.1956 | | Raith Rovers | – | Airdrieonians | | 4:2 |
| |
Scottish League Cup 1955, Group 2 |
| 27.08.1955 | | East Fife | – | Raith Rovers | | 0:2 |
| |
Scottish League Cup 1954, Group 1 |
| 04.09.1954 | | Raith Rovers | – | Motherwell | | 3:0 |
| |
Scottish League Cup 1953, Group 3 |
| 29.08.1953 | | Raith Rovers | – | Hearts | | 3:1 |
| |
Scottish League Cup 1953, Group 3 |
| 26.08.1953 | | Raith Rovers | – | Hamilton Academical | | 2:0 |
| |
Scottish League Cup 1953, Group 3 |
| 12.08.1953 | | Hamilton Academical | – | Raith Rovers | | 1:2 |
| |
Scottish League Cup 1952, Group 4 |
| 16.08.1952 | | Airdrieonians | – | Raith Rovers | | 0:1 |
| |
Scottish League Cup 1952, Group 4 |
| 13.08.1952 | | Raith Rovers | – | Clyde | | 4:3 |
| |
Scottish League Cup 1951, Group 3 |
| 25.08.1951 | | Raith Rovers | – | Hearts | | 2:0 |
| |
Scottish League Cup 1951, Group 3 |
| 15.08.1951 | | Raith Rovers | – | St. Mirren | | 3:2 |
| |
Scottish League Cup 1950, Group 1 |
| 12.08.1950 | | Raith Rovers | – | Third Lanark | | 3:2 |
| |
Scottish League Cup 1949, Group 4 |
| 20.08.1949 | | Raith Rovers | – | Stirling Albion | | 6:2 |
| |
Scottish League Cup 1948, Semifinal |
| 20.11.1948 | | Raith Rovers | – | Hamilton Academical | | 2:0 |
| |
Scottish League Cup 1948, Quarterfinal |
| 30.10.1948 | | Raith Rovers | – | East Fife | | 5:3 |
| |
Scottish League Cup 1948, Group 5 |
| 09.10.1948 | | Raith Rovers | – | Stirling Albion | | 6:2 |
| |
Scottish League Cup 1948, Group 5 |
| 02.10.1948 | | Cowdenbeath | – | Raith Rovers | | 0:6 |
| |
Scottish League Cup 1948, Group 5 |
| 25.09.1948 | | Raith Rovers | – | Dunfermline Athletic | | 2:1 |
| |
Scottish League Cup 1948, Group 5 |
| 18.09.1948 | | Stirling Albion | – | Raith Rovers | | 1:7 |
| |
Scottish League Cup 1947, Group 5 |
| 06.09.1947 | | Alloa Athletic | – | Raith Rovers | | 1:2 |
| |
Scottish League Cup 1947, Group 5 |
| 30.08.1947 | | Raith Rovers | – | Dunfermline Athletic | | 6:1 |
| |
Scottish League Cup 1947, Group 5 |
| 23.08.1947 | | Raith Rovers | – | Hamilton Academical | | 3:1 |
| |
Scottish League Cup 1947, Group 5 |
| 16.08.1947 | | Raith Rovers | – | Alloa Athletic | | 4:2 |
| |
Scottish League Cup 1947, Group 5 |
| 09.08.1947 | | Dunfermline Athletic | – | Raith Rovers | | 0:2 |
| |
Scottish League Cup 1946/47, Section 6 |
| 05.10.1946 | | Stenhousemuir | – | Raith Rovers | | 1:2 |
| |
