Scottish League Cup 2023/24, Group F |
 | 26.07.2023 |  | Kilmarnock | – | Raith Rovers | | 2:2 (1:0),
pen. 4:5 |
| Kilmarnock |
Scottish League Cup 2022/23, Group B |
| 13.07.2022 | | Kilmarnock | – | Partick Thistle | | 1:1 (1:1),
pen. 4:5 |
| Kilmarnock |
Scottish League Cup 2021/22, Group G |
| 20.07.2021 | | Kilmarnock | – | Greenock Morton | | 1:1 (0:1),
pen. 4:3 |
| Kilmarnock |
Scottish League Cup 2019/20, Quarterfinal |
| 25.09.2019 | | Kilmarnock | – | Hibernian | | 0:0 aet,
pen. 4:5 |
| Kilmarnock |
Scottish League Cup 2018/19, Group H |
| 13.07.2018 | | Kilmarnock | – | St. Mirren | | 0:0,
pen. 2:3 |
| Kilmarnock |
Scottish League Cup 2016/17, First Round, Group H |
| 30.07.2016 | | Kilmarnock | – | Albion Rovers | | 0:0,
pen. 3:5 |
| Kilmarnock |
Scottish League Cup 2002/03, Second Round |
| 24.09.2002 | | Kilmarnock | – | Airdrie United | | 0:0 aet,
pen. 3:4 |
| |
Scottish League Cup 2001/02, Third Round |
| 09.10.2001 | | Ayr United | – | Kilmarnock | | 0:0 aet,
pen. 5:4 |
| |
Scottish League Cup 1984, Third Round |
| 29.08.1984 | | Dundee | – | Kilmarnock | | 1:1 aet,
pen. 3:2 |
| |
Scottish League Cup 1984, Second Round |
| 21.08.1984 | | Kilmarnock | – | Alloa Athletic | | 1:1 aet,
pen. 3:2 |
| |
Scottish League Cup 1983/84, Group 4 |
| 05.10.1983 | | Celtic | – | Kilmarnock | | 1:1 |
| |
Scottish League Cup 1982, Group 8 |
| 18.08.1982 | | Hamilton Academical | – | Kilmarnock | | 0:0 |
| |
Scottish League Cup 1981, Group 3 |
| 15.08.1981 | | Hearts | – | Kilmarnock | | 1:1 |
| |
Scottish League Cup 1981, Group 3 |
| 12.08.1981 | | Kilmarnock | – | Airdrieonians | | 1:1 |
| |
Scottish League Cup 1980, Third Round |
| 24.09.1980 | | Kilmarnock | – | Dundee | | 0:0 aet,
pen. 3:5 |
| |
Scottish League Cup 1980, Third Round |
| 03.09.1980 | | Dundee | – | Kilmarnock | | 0:0 |
| |
Scottish League Cup 1980, Second Round |
| 27.08.1980 | | Kilmarnock | – | Dunfermline Athletic | | 0:0 |
| |
Scottish League Cup 1979, Second Round |
| 01.09.1979 | | Forfar Athletic | – | Kilmarnock | | 1:1 |
| |
Scottish League Cup 1979, First Round |
| 22.08.1979 | | Alloa Athletic | – | Kilmarnock | | 1:1 aet |
| |
Scottish League Cup 1978/79, Second Round |
| 02.09.1978 | | Alloa Athletic | – | Kilmarnock | | 1:1 |
| |
Scottish League Cup 1977/78, Second Round |
| 31.08.1977 | | Kilmarnock | – | St. Mirren | | 0:0 |
| |
Scottish League Cup 1976, Group 2 |
| 21.08.1976 | | Kilmarnock | – | St. Mirren | | 1:1 |
| |
Scottish League Cup 1974, Quarterfinal |
| 11.09.1974 | | Kilmarnock | – | Hibernian | | 3:3 |
| |
Scottish League Cup 1974, Group 6 |
| 28.08.1974 | | Montrose | – | Kilmarnock | | 1:1 |
| |
Scottish League Cup 1973, Group 5 |
| 25.08.1973 | | Queen's Park | – | Kilmarnock | | 1:1 |
| |
Scottish League Cup 1973, Group 5 |
| 15.08.1973 | | Kilmarnock | – | Hamilton Academical | | 0:0 |
| |
Scottish League Cup 1972, Group 4 |
| 12.08.1972 | | Stenhousemuir | – | Kilmarnock | | 1:1 |
| |
Scottish League Cup 1971, Group 1 |
| 01.09.1971 | | Kilmarnock | – | Hibernian | | 0:0 |
| |
Scottish League Cup 1970, Group 3 |
| 22.08.1970 | | Ayr United | – | Kilmarnock | | 0:0 |
| |
Scottish League Cup 1969, Group 3 |
| 16.08.1969 | | Dundee | – | Kilmarnock | | 0:0 |
| |
Scottish League Cup 1968/69, Group 2 |
| 31.08.1968 | | Hearts | – | Kilmarnock | | 0:0 |
| |
Scottish League Cup 1968/69, Group 2 |
| 24.08.1968 | | Kilmarnock | – | Dundee | | 2:2 |
| |
Scottish League Cup 1968/69, Group 2 |
| 17.08.1968 | | Kilmarnock | – | Hearts | | 3:3 |
| |
Scottish League Cup 1967, Group 1 |
| 30.08.1967 | | Kilmarnock | – | Airdrieonians | | 0:0 |
| |
Scottish League Cup 1967, Group 1 |
| 12.08.1967 | | Kilmarnock | – | Dunfermline Athletic | | 2:2 |
| |
Scottish League Cup 1966, Group 2 |
| 27.08.1966 | | Stirling Albion | – | Kilmarnock | | 0:0 |
| |
Scottish League Cup 1966, Group 2 |
| 20.08.1966 | | Rangers | – | Kilmarnock | | 0:0 |
| |
Scottish League Cup 1965, Quarterfinal |
| 22.09.1965 | | Ayr United | – | Kilmarnock | | 2:2 |
| |
Scottish League Cup 1964, Group 3 |
| 12.08.1964 | | Partick Thistle | – | Kilmarnock | | 0:0 |
| |
Scottish League Cup 1964, Group 3 |
| 08.08.1964 | | Kilmarnock | – | Hearts | | 1:1 |
| |
Scottish League Cup 1963, Group 4 |
| 31.08.1963 | | Rangers | – | Kilmarnock | | 2:2 |
| |
Scottish League Cup 1963, Group 4 |
| 14.08.1963 | | Kilmarnock | – | Celtic | | 0:0 |
| |
Scottish League Cup 1962, Group 1 |
| 15.08.1962 | | Dunfermline Athletic | – | Kilmarnock | | 3:3 |
| |
Scottish League Cup 1960, Group 3 |
| 27.08.1960 | | Hibernian | – | Kilmarnock | | 2:2 |
| |
Scottish League Cup 1959, Group 3 |
| 12.08.1959 | | Stirling Albion | – | Kilmarnock | | 2:2 |
| |
Scottish League Cup 1958, Quarterfinal |
| 16.09.1958 | | Dunfermline Athletic | – | Kilmarnock | | 3:3 |
| |
Scottish League Cup 1957, Group 4 |
| 31.08.1957 | | Queen's Park | – | Kilmarnock | | 2:2 |
| |
Scottish League Cup 1957, Group 4 |
| 28.08.1957 | | Kilmarnock | – | Dundee | | 1:1 |
| |
Scottish League Cup 1957, Group 4 |
| 24.08.1957 | | Hearts | – | Kilmarnock | | 1:1 |
| |
Scottish League Cup 1956, Group 3 |
| 15.08.1956 | | St. Mirren | – | Kilmarnock | | 2:2 |
| |
Scottish League Cup 1956, Group 3 |
| 11.08.1956 | | Kilmarnock | – | Dunfermline Athletic | | 0:0 |
| |
Scottish League Cup 1955, Group 1 |
| 03.09.1955 | | Airdrieonians | – | Kilmarnock | | 3:3 |
| |
Scottish League Cup 1955, Group 1 |
| 31.08.1955 | | Kilmarnock | – | Dundee | | 0:0 |
| |
Scottish League Cup 1955, Group 1 |
| 13.08.1955 | | Kilmarnock | – | St. Mirren | | 0:0 |
| |
Scottish League Cup 1954, Group 1 |
| 21.08.1954 | | Kilmarnock | – | St. Mirren | | 2:2 |
| |
Scottish League Cup 1950, Group 5 |
| 02.09.1950 | | Kilmarnock | – | Dumbarton | | 0:0 |
| |
Scottish League Cup 1950, Group 5 |
| 16.08.1950 | | Ayr United | – | Kilmarnock | | 2:2 |
| |
Scottish League Cup 1948, Group 6 |
| 09.10.1948 | | Queen's Park | – | Kilmarnock | | 2:2 |
| |
Scottish League Cup 1948, Group 6 |
| 18.09.1948 | | Kilmarnock | – | Queen's Park | | 3:3 |
| |
Scottish League Cup 1947, Group 8 |
| 16.08.1947 | | Kilmarnock | – | East Fife | | 0:0 |
| |
Scottish League Cup 1947, Group 8 |
| 09.08.1947 | | Ayr United | – | Kilmarnock | | 2:2 |
| |
