Scottish League Cup 2023/24, Group F |
 | 26.07.2023 |  | Kilmarnock | – | Raith Rovers | | 2:2 (1:0),
pen. 4:5 |
| Kilmarnock |
Scottish League Cup 2023/24, Group F |
| 15.07.2023 | | Raith Rovers | – | Dunfermline Athletic | | 1:1 (1:1),
pen. 2:4 |
| Kirkcaldy |
Scottish League Cup 2022/23, Group A |
| 19.07.2022 | | Dumbarton | – | Raith Rovers | | 0:0,
pen. 2:3 |
| Dumbarton |
Scottish League Cup 2022/23, Group A |
| 16.07.2022 | | Raith Rovers | – | Stirling Albion | | 1:1 (1:1),
pen. 4:5 |
| Kirkcaldy |
Scottish League Cup 2021/22, Group D |
| 24.07.2021 | | Raith Rovers | – | Alloa Athletic | | 0:0,
pen. 5:4 |
| Kirkcaldy |
Scottish League Cup 2021/22, Group D |
| 21.07.2021 | | Livingston | – | Raith Rovers | | 0:0,
pen. 6:5 |
| Livingston |
Scottish League Cup 2020/21, Group A |
| 10.11.2020 | | Raith Rovers | – | Inverness | | 3:3 (1:1),
pen. 3:2 |
| Kirkcaldy |
Scottish League Cup 2018/19, Group C |
| 21.07.2018 | | Raith Rovers | – | Hearts | | 1:1 (0:0),
pen. 2:4 |
| Methil |
Scottish League Cup 2016/17, First Round, Group D |
| 23.07.2016 | | Ross County | – | Raith Rovers | | 1:1 (0:1),
pen. 3:4 |
| Dingwall |
Scottish League Cup 2013/14, Second Round |
| 27.08.2013 | | Raith Rovers | – | Hearts | | 1:1 aet
(0:0, 1:1),
pen. 4:5 |
| Kirkcaldy |
Scottish League Cup 2008/09, First Round |
| 05.08.2008 | | Albion Rovers | – | Raith Rovers | | 0:0 aet,
pen. 3:4 |
| Coatbridge |
Scottish League Cup 1999/00, Second Round |
| 18.08.1999 | | Raith Rovers | – | Motherwell | | 2:2 aet,
pen. 4:5 |
| |
Scottish League Cup 1994, Final |
| 27.11.1994 | | Raith Rovers | – | Celtic | | 2:2 aet
(1:1, 2:2),
pen. 6:5 |
| Glasgow |
Scottish League Cup 1994, Semifinal |
| 25.10.1994 | | Raith Rovers | – | Airdrieonians | | 1:1 aet,
pen. 4:5 |
| Perth |
Scottish League Cup 1988, Second Round |
| 17.08.1988 | | Falkirk | – | Raith Rovers | | 1:1 aet,
pen. 9:8 |
| |
Scottish League Cup 1982, Group 4 |
| 25.08.1982 | | Raith Rovers | – | St. Johnstone | | 3:3 |
| |
Scottish League Cup 1982, Group 4 |
| 14.08.1982 | | Raith Rovers | – | Falkirk | | 0:0 |
| |
Scottish League Cup 1981, Group 2 |
| 22.08.1981 | | Raith Rovers | – | Dundee | | 1:1 |
| |
Scottish League Cup 1980, Second Round |
| 30.08.1980 | | Raith Rovers | – | Dumbarton | | 1:1 aet |
| |
Scottish League Cup 1979, Quarterfinal |
| 31.10.1979 | | Dundee United | – | Raith Rovers | | 0:0 |
| |
Scottish League Cup 1979, Third Round |
| 26.09.1979 | | Raith Rovers | – | St. Johnstone | | 1:1 |
| |
Scottish League Cup 1976, Group 5 |
| 01.09.1976 | | Raith Rovers | – | Clyde | | 1:1 |
| |
Scottish League Cup 1976, Group 5 |
| 14.08.1976 | | Clyde | – | Raith Rovers | | 1:1 |
| |
Scottish League Cup 1975, Group 6 |
| 23.08.1975 | | St. Mirren | – | Raith Rovers | | 1:1 |
| |
Scottish League Cup 1975, Group 6 |
| 13.08.1975 | | East Fife | – | Raith Rovers | | 2:2 |
| |
Scottish League Cup 1974, Group 5 |
| 10.08.1974 | | Raith Rovers | – | Queen of the South | | 1:1 |
| |
Scottish League Cup 1973, Group 6 |
| 18.08.1973 | | Raith Rovers | – | Queen of the South | | 2:2 |
| |
Scottish League Cup 1971, Group 7 |
| 28.08.1971 | | East Fife | – | Raith Rovers | | 1:1 |
| |
Scottish League Cup 1971, Group 7 |
| 25.08.1971 | | Raith Rovers | – | Arbroath | | 1:1 |
| |
Scottish League Cup 1971, Group 7 |
| 21.08.1971 | | Raith Rovers | – | Partick Thistle | | 1:1 |
| |
Scottish League Cup 1969, Group 1 |
| 23.08.1969 | | Rangers | – | Raith Rovers | | 3:3 |
| |
Scottish League Cup 1968/69, Group 1 |
| 17.08.1968 | | St. Johnstone | – | Raith Rovers | | 0:0 |
| |
Scottish League Cup 1968/69, Group 1 |
| 10.08.1968 | | Falkirk | – | Raith Rovers | | 1:1 |
| |
Scottish League Cup 1967, Group 7 |
| 26.08.1967 | | Dumbarton | – | Raith Rovers | | 1:1 |
| |
Scottish League Cup 1966, Group 5 |
| 20.08.1966 | | Berwick Rangers | – | Raith Rovers | | 1:1 |
| |
Scottish League Cup 1966, Group 5 |
| 17.08.1966 | | Ayr United | – | Raith Rovers | | 0:0 |
| |
Scottish League Cup 1965, Group 6 |
| 21.08.1965 | | Queen's Park | – | Raith Rovers | | 1:1 |
| |
Scottish League Cup 1965, Group 6 |
| 18.08.1965 | | Arbroath | – | Raith Rovers | | 2:2 |
| |
Scottish League Cup 1964, Group 5 |
| 15.08.1964 | | Queen of the South | – | Raith Rovers | | 1:1 |
| |
Scottish League Cup 1963, Group 8 |
| 10.08.1963 | | Raith Rovers | – | East Fife | | 1:1 |
| |
Scottish League Cup 1962, Group 1 |
| 25.08.1962 | | Dunfermline Athletic | – | Raith Rovers | | 1:1 |
| |
Scottish League Cup 1962, Group 1 |
| 15.08.1962 | | Airdrieonians | – | Raith Rovers | | 1:1 |
| |
Scottish League Cup 1962, Group 1 |
| 11.08.1962 | | Raith Rovers | – | Dunfermline Athletic | | 2:2 |
| |
Scottish League Cup 1960, Group 4 |
| 20.08.1960 | | Raith Rovers | – | Ayr United | | 1:1 |
| |
Scottish League Cup 1959, Quarterfinal |
| 09.09.1959 | | Raith Rovers | – | Arbroath | | 2:2 |
| |
Scottish League Cup 1956, Group 1 |
| 29.08.1956 | | Raith Rovers | – | Dundee | | 2:2 |
| |
Scottish League Cup 1954, Group 1 |
| 21.08.1954 | | Motherwell | – | Raith Rovers | | 1:1 |
| |
Scottish League Cup 1954, Group 1 |
| 18.08.1954 | | Raith Rovers | – | St. Mirren | | 2:2 |
| |
Scottish League Cup 1952, Group 4 |
| 30.08.1952 | | Raith Rovers | – | Airdrieonians | | 1:1 |
| |
Scottish League Cup 1950, Group 1 |
| 02.09.1950 | | Raith Rovers | – | Celtic | | 2:2 |
| |
Scottish League Cup 1950, Group 1 |
| 16.08.1950 | | East Fife | – | Raith Rovers | | 3:3 |
| |
Scottish League Cup 1948, Group 5 |
| 11.09.1948 | | Raith Rovers | – | Cowdenbeath | | 3:3 |
| |
