Scottish League Cup 2023/24, Group G |
 | 18.07.2023 |  | Queen of the South | – | Motherwell | | 3:3 (1:1),
pen. 4:5 |
| Dumfries |
Scottish League Cup 2018/19, Group G |
| 21.07.2018 | | Stranraer | – | Motherwell | | 1:1 (0:1),
pen. 3:2 |
| Stranraer |
Scottish League Cup 2014/15, Third Round |
| 24.09.2014 | | Hamilton Academical | – | Motherwell | | 0:0 aet,
pen. 6:5 |
| Hamilton |
Scottish League Cup 2011/12, Third Round |
| 20.09.2011 | | Motherwell | – | Hibernian | | 2:2 aet
(2:1, 2:2),
pen. 6:7 |
| Motherwell |
Scottish League Cup 2009/10, Third Round |
| 22.09.2009 | | Motherwell | – | Inverness | | 1:1 aet
(1:0, 1:1) |
| Motherwell |
Scottish League Cup 2003/04, Second Round |
| 23.09.2003 | | Forfar Athletic | – | Motherwell | | 3:3 aet
(1:1, 2:2),
pen. 4:2 |
| |
Scottish League Cup 1999/00, Second Round |
| 18.08.1999 | | Raith Rovers | – | Motherwell | | 2:2 aet,
pen. 4:5 |
| |
Scottish League Cup 1997, Second Round |
| 09.08.1997 | | Motherwell | – | Inverness | | 2:2 aet,
pen. 4:1 |
| |
Scottish League Cup 1996, Second Round |
| 13.08.1996 | | Motherwell | – | Alloa Athletic | | 0:0 aet,
pen. 2:4 |
| |
Scottish League Cup 1995, Second Round |
| 19.08.1995 | | Clydebank | – | Motherwell | | 1:1 aet,
pen. 1:4 |
| |
Scottish League Cup 1986, Semifinal |
| 23.09.1986 | | Motherwell | – | Celtic | | 2:2 aet,
pen. 4:5 |
| |
Scottish League Cup 1983/84, Group 1 |
| 26.10.1983 | | Motherwell | – | Alloa Athletic | | 2:2 |
| |
Scottish League Cup 1982, Group 5 |
| 21.08.1982 | | Motherwell | – | Forfar Athletic | | 1:1 |
| |
Scottish League Cup 1982, Group 5 |
| 18.08.1982 | | Clyde | – | Motherwell | | 3:3 |
| |
Scottish League Cup 1981, Group 4 |
| 26.08.1981 | | Dundee United | – | Motherwell | | 1:1 |
| |
Scottish League Cup 1980, Second Round |
| 27.08.1980 | | Stenhousemuir | – | Motherwell | | 0:0 |
| |
Scottish League Cup 1977/78, Second Round |
| 31.08.1977 | | Celtic | – | Motherwell | | 0:0 |
| |
Scottish League Cup 1976, Group 1 |
| 25.08.1976 | | Motherwell | – | Dundee | | 3:3 |
| |
Scottish League Cup 1976, Group 1 |
| 14.08.1976 | | Motherwell | – | Partick Thistle | | 1:1 |
| |
Scottish League Cup 1975, Group 1 |
| 23.08.1975 | | Motherwell | – | Rangers | | 2:2 |
| |
Scottish League Cup 1975, Group 1 |
| 16.08.1975 | | Rangers | – | Motherwell | | 1:1 |
| |
Scottish League Cup 1974, Group 4 |
| 28.08.1974 | | Motherwell | – | Celtic | | 2:2 |
| |
Scottish League Cup 1974, Group 4 |
| 14.08.1974 | | Motherwell | – | Dundee United | | 0:0 |
| |
Scottish League Cup 1973, Group 4 |
| 29.08.1973 | | Motherwell | – | Aberdeen | | 0:0 |
| |
Scottish League Cup 1972, Second Round |
| 04.10.1972 | | Airdrieonians | – | Motherwell | | 1:1 |
| |
Scottish League Cup 1972, Group 7 |
| 26.08.1972 | | Motherwell | – | Clyde | | 1:1 |
| |
Scottish League Cup 1972, Group 7 |
| 12.08.1972 | | Clyde | – | Motherwell | | 2:2 |
| |
Scottish League Cup 1971, Group 1 |
| 21.08.1971 | | Dundee United | – | Motherwell | | 2:2 |
| |
Scottish League Cup 1970, Group 2 |
| 26.08.1970 | | Dunfermline Athletic | – | Motherwell | | 1:1 |
| |
Scottish League Cup 1969, Group 5 |
| 23.08.1969 | | East Fife | – | Motherwell | | 0:0 |
| |
Scottish League Cup 1968/69, Group 7 |
| 24.08.1968 | | Motherwell | – | Hamilton Academical | | 0:0 |
| |
Scottish League Cup 1967, Group 3 |
| 12.08.1967 | | Motherwell | – | Clyde | | 2:2 |
| |
Scottish League Cup 1966, Group 3 |
| 03.09.1966 | | Partick Thistle | – | Motherwell | | 0:0 |
| |
Scottish League Cup 1966, Group 3 |
| 17.08.1966 | | Motherwell | – | Falkirk | | 2:2 |
| |
Scottish League Cup 1964, Group 4 |
| 08.08.1964 | | Falkirk | – | Motherwell | | 1:1 |
| |
Scottish League Cup 1963, Quarterfinal |
| 11.09.1963 | | Motherwell | – | Morton | | 0:0 |
| |
Scottish League Cup 1963, Group 1 |
| 28.08.1963 | | Hearts | – | Motherwell | | 0:0 |
| |
Scottish League Cup 1962, Group 3 |
| 18.08.1962 | | Partick Thistle | – | Motherwell | | 1:1 |
| |
Scottish League Cup 1961, Quarterfinal |
| 20.09.1961 | | St. Johnstone | – | Motherwell | | 1:1 |
| |
Scottish League Cup 1961, Group 2 |
| 19.08.1961 | | Motherwell | – | Dunfermline Athletic | | 1:1 |
| |
Scottish League Cup 1960, Group 1 |
| 27.08.1960 | | Clyde | – | Motherwell | | 1:1 |
| |
Scottish League Cup 1960, Group 1 |
| 13.08.1960 | | Motherwell | – | Clyde | | 4:4 |
| |
Scottish League Cup 1959, Quarterfinal |
| 09.09.1959 | | Motherwell | – | Hearts | | 1:1 |
| |
Scottish League Cup 1958, Group 3 |
| 30.08.1958 | | Partick Thistle | – | Motherwell | | 1:1 |
| |
Scottish League Cup 1955, Semifinal |
| 01.10.1955 | | St. Mirren | – | Motherwell | | 3:3 aet |
| |
Scottish League Cup 1954, Quarterfinal |
| 25.09.1954 | | Rangers | – | Motherwell | | 1:1 |
| |
Scottish League Cup 1954, Group 1 |
| 21.08.1954 | | Motherwell | – | Raith Rovers | | 1:1 |
| |
Scottish League Cup 1954, Group 1 |
| 14.08.1954 | | St. Mirren | – | Motherwell | | 4:4 |
| |
Scottish League Cup 1952, Group 3 |
| 27.08.1952 | | Motherwell | – | Rangers | | 3:3 |
| |
Scottish League Cup 1951, Group 2 |
| 18.08.1951 | | Partick Thistle | – | Motherwell | | 0:0 |
| |
Scottish League Cup 1949, Group 3 |
| 03.09.1949 | | Motherwell | – | Clyde | | 1:1 |
| |
Scottish League Cup 1949, Group 3 |
| 27.08.1949 | | Motherwell | – | Partick Thistle | | 1:1 |
| |
Scottish League Cup 1949, Group 3 |
| 20.08.1949 | | Clyde | – | Motherwell | | 2:2 |
| |
Scottish League Cup 1946/47, Section 4 |
| 28.09.1946 | | Falkirk | – | Motherwell | | 1:1 |
| |
