Scottish League Cup 2021/22, Second round |
 | 14.08.2021 |  | Ayr United | – | Dundee United | | 1:1 aet
(0:0, 1:1),
pen. 3:4 |
| Ayr |
Scottish League Cup 2020/21, Group C |
| 10.11.2020 | | St. Johnstone | – | Dundee United | | 0:0,
pen. 3:4 |
| Perth |
Scottish League Cup 2019/20, Group A |
| 12.07.2019 | | Hearts | – | Dundee United | | 1:1 (1:1),
pen. 5:3 |
| Edinburgh |
Scottish League Cup 2018/19, Group A |
| 21.07.2018 | | Dundee United | – | Alloa Athletic | | 1:1 (1:0),
pen. 3:4 |
| Dundee |
Scottish League Cup 2018/19, Group A |
| 14.07.2018 | | Dundee United | – | Arbroath | | 1:1 (0:0),
pen. 3:5 |
| Dundee |
Scottish League Cup 2017/18, Group C |
| 30.07.2017 | | Dundee | – | Dundee United | | 1:1 (0:1),
pen. 3:4 |
| Dundee |
Scottish League Cup 2016/17, First Round, Group C |
| 23.07.2016 | | Inverness | – | Dundee United | | 1:1 (1:1),
pen. 1:4 |
| Inverness |
Scottish League Cup 2016/17, First Round, Group C |
| 15.07.2016 | | Arbroath | – | Dundee United | | 1:1 (0:0),
pen. 3:5 |
| Arbroath |
Scottish League Cup 2014/15, Quarterfinal |
| 29.10.2014 | | Hibernian | – | Dundee United | | 3:3 aet
(1:2, 3:3),
pen. 6:7 |
| Edinburgh |
Scottish League Cup 2012/13, Quarterfinal |
| 31.10.2012 | | Dundee United | – | Hearts | | 1:1 aet
(1:1, 1:1),
pen. 4:5 |
| Dundee |
Scottish League Cup 2011/12, Quarterfinal |
| 25.10.2011 | | Dundee United | – | Falkirk | | 2:2 aet
(0:0, 1:1),
pen. 4:5 |
| Dundee |
Scottish League Cup 2008/09, Semifinal |
| 28.01.2009 | | Celtic | – | Dundee United | | 0:0 aet,
pen. 11:10 |
| Glasgow |
Scottish League Cup 2007/08, Final |
| 16.03.2008 | | Dundee United | – | Rangers | | 2:2 aet
(1:0, 1:1),
pen. 2:3 |
| Glasgow |
Scottish League Cup 2000/01, Third Round |
| 05.09.2000 | | Dundee United | – | Airdrieonians | | 0:0 aet,
pen. 4:3 |
| |
Scottish League Cup 1998, Second Round |
| 08.08.1998 | | Dundee United | – | Stirling Albion | | 2:2 aet,
pen. 3:0 |
| |
Scottish League Cup 1996, Third Round |
| 03.09.1996 | | Dundee United | – | Dundee | | 2:2 aet,
pen. 2:4 |
| |
Scottish League Cup 1994, Third Round |
| 31.08.1994 | | Hamilton Academical | – | Dundee United | | 2:2 aet,
pen. 5:3 |
| |
Scottish League Cup 1993, Quarterfinal |
| 31.08.1993 | | Dundee United | – | Falkirk | | 3:3 aet,
pen. 4:2 |
| Dundee |
Scottish League Cup 1983/84, Semifinal |
| 14.02.1984 | | Dundee United | – | Rangers | | 1:1 |
| |
Scottish League Cup 1983/84, Group 1 |
| 07.09.1983 | | Morton | – | Dundee United | | 1:1 |
| |
Scottish League Cup 1981, Group 4 |
| 26.08.1981 | | Dundee United | – | Motherwell | | 1:1 |
| |
Scottish League Cup 1980, Semifinal |
| 12.11.1980 | | Dundee United | – | Celtic | | 1:1 |
| |
Scottish League Cup 1979, Final |
| 08.12.1979 | | Dundee United | – | Aberdeen | | 0:0 |
| Dundee |
Scottish League Cup 1979, Quarterfinal |
| 31.10.1979 | | Dundee United | – | Raith Rovers | | 0:0 |
| |
Scottish League Cup 1977/78, Second Round |
| 31.08.1977 | | Partick Thistle | – | Dundee United | | 0:0 |
| |
Scottish League Cup 1976, Group 3 |
| 01.09.1976 | | Celtic | – | Dundee United | | 1:1 |
| |
Scottish League Cup 1976, Group 3 |
| 28.08.1976 | | Dundee United | – | Dumbarton | | 1:1 |
| |
Scottish League Cup 1974, Group 4 |
| 28.08.1974 | | Ayr United | – | Dundee United | | 2:2 |
| |
Scottish League Cup 1974, Group 4 |
| 14.08.1974 | | Motherwell | – | Dundee United | | 0:0 |
| |
Scottish League Cup 1973, Group 4 |
| 15.08.1973 | | Dundee United | – | Aberdeen | | 0:0 |
| |
Scottish League Cup 1972, Second Round |
| 04.10.1972 | | Hibernian | – | Dundee United | | 0:0 |
| |
Scottish League Cup 1971, Group 1 |
| 21.08.1971 | | Dundee United | – | Motherwell | | 2:2 |
| |
Scottish League Cup 1970, Group 1 |
| 26.08.1970 | | Dundee United | – | Celtic | | 2:2 |
| |
Scottish League Cup 1970, Group 1 |
| 22.08.1970 | | Dundee United | – | Clyde | | 1:1 |
| |
Scottish League Cup 1970, Group 1 |
| 19.08.1970 | | Hearts | – | Dundee United | | 0:0 |
| |
Scottish League Cup 1970, Group 1 |
| 15.08.1970 | | Celtic | – | Dundee United | | 2:2 |
| |
Scottish League Cup 1970, Group 1 |
| 08.08.1970 | | Clyde | – | Dundee United | | 1:1 |
| |
Scottish League Cup 1967, Group 2 |
| 30.08.1967 | | Aberdeen | – | Dundee United | | 2:2 |
| |
Scottish League Cup 1966, Group 1 |
| 27.08.1966 | | Dundee | – | Dundee United | | 1:1 |
| |
Scottish League Cup 1966, Group 1 |
| 17.08.1966 | | St. Johnstone | – | Dundee United | | 1:1 |
| |
Scottish League Cup 1965, Group 1 |
| 18.08.1965 | | Dundee | – | Dundee United | | 0:0 |
| |
Scottish League Cup 1963, Group 2 |
| 10.08.1963 | | Dundee United | – | Aberdeen | | 1:1 |
| |
Scottish League Cup 1962, Group 2 |
| 01.09.1962 | | Dundee United | – | Celtic | | 0:0 |
| |
Scottish League Cup 1961, Group 2 |
| 02.09.1961 | | Aberdeen | – | Dundee United | | 2:2 |
| |
Scottish League Cup 1961, Group 2 |
| 16.08.1961 | | Dundee United | – | Dunfermline Athletic | | 0:0 |
| |
Scottish League Cup 1960, Group 8 |
| 03.09.1960 | | Stenhousemuir | – | Dundee United | | 1:1 |
| |
Scottish League Cup 1960, Group 8 |
| 20.08.1960 | | Dundee United | – | Stenhousemuir | | 3:3 |
| |
Scottish League Cup 1959, Supplementary Round |
| 31.08.1959 | | Falkirk | – | Dundee United | | 1:1 |
| |
Scottish League Cup 1959, Group 9 |
| 12.08.1959 | | Montrose | – | Dundee United | | 1:1 |
| |
Scottish League Cup 1956, Group 8 |
| 25.08.1956 | | Ayr United | – | Dundee United | | 1:1 |
| |
Scottish League Cup 1955, Group 7 |
| 27.08.1955 | | Albion Rovers | – | Dundee United | | 3:3 |
| |
Scottish League Cup 1953, Group 7 |
| 22.08.1953 | | Dundee United | – | Morton | | 2:2 |
| |
Scottish League Cup 1951, Group 5 |
| 15.08.1951 | | Stenhousemuir | – | Dundee United | | 1:1 |
| |
Scottish League Cup 1951, Group 5 |
| 11.08.1951 | | Dundee United | – | Cowdenbeath | | 1:1 |
| |
Scottish League Cup 1950, Group 6 |
| 19.08.1950 | | Cowdenbeath | – | Dundee United | | 2:2 |
| |
Scottish League Cup 1948, Group 7 |
| 11.09.1948 | | St. Johnstone | – | Dundee United | | 1:1 |
| |
Scottish League Cup 1947, Group 6 |
| 16.08.1947 | | Dundee United | – | Leith Athletic | | 2:2 |
| |
Scottish League Cup 1946/47, Quarterfinal |
| 05.03.1947 | | Dundee United | – | Rangers | | 1:1 |
| |
