Scottish League Cup 2020/21, Group H |
 | 10.10.2020 |  | Edinburgh City | – | Stenhousemuir | | 2:2 (1:1),
pen. 2:4 |
| Edinburgh |
Scottish League Cup 2017/18, Group G |
| 18.07.2017 | | Albion Rovers | – | Stenhousemuir | | 1:1 (0:1),
pen. 2:3 |
| Coatbridge |
Scottish League Cup 2012/13, Third Round |
| 25.09.2012 | | Stenhousemuir | – | Inverness | | 1:1 aet
(1:1, 1:1),
pen. 5:6 |
| Stenhousemuir |
Scottish League Cup 2011/12, First Round |
| 30.07.2011 | | Cowdenbeath | – | Stenhousemuir | | 2:2 aet,
pen. 3:4 |
| Cowdenbeath |
Scottish League Cup 2002/03, First Round |
| 11.09.2002 | | Stirling Albion | – | Stenhousemuir | | 3:3 aet,
pen. 4:2 |
| |
Scottish League Cup 2001/02, First Round |
| 11.09.2001 | | Clyde | – | Stenhousemuir | | 2:2 aet,
pen. 4:2 |
| |
Scottish League Cup 1996, Second Round |
| 14.08.1996 | | Hearts | – | Stenhousemuir | | 1:1 aet,
pen. 5:4 |
| |
Scottish League Cup 1983/84, First Round |
| 17.08.1983 | | Stenhousemuir | – | Forfar Athletic | | 2:2 |
| |
Scottish League Cup 1982, Group 9 |
| 28.08.1982 | | Cowdenbeath | – | Stenhousemuir | | 1:1 |
| |
Scottish League Cup 1982, Group 9 |
| 21.08.1982 | | Albion Rovers | – | Stenhousemuir | | 0:0 |
| |
Scottish League Cup 1982, Group 9 |
| 18.08.1982 | | Stenhousemuir | – | Montrose | | 2:2 |
| |
Scottish League Cup 1982, Group 9 |
| 14.08.1982 | | Stenhousemuir | – | Meadowbank Thistle | | 1:1 |
| |
Scottish League Cup 1981, Group 9 |
| 19.08.1981 | | Meadowbank Thistle | – | Stenhousemuir | | 1:1 |
| |
Scottish League Cup 1980, Second Round |
| 27.08.1980 | | Stenhousemuir | – | Motherwell | | 0:0 |
| |
Scottish League Cup 1976, Group 9 |
| 28.08.1976 | | Stenhousemuir | – | Berwick Rangers | | 0:0 |
| |
Scottish League Cup 1976, Group 9 |
| 18.08.1976 | | Stenhousemuir | – | Meadowbank Thistle | | 1:1 |
| |
Scottish League Cup 1975, Group 8 |
| 13.08.1975 | | Stenhousemuir | – | Albion Rovers | | 0:0 |
| |
Scottish League Cup 1975, Group 8 |
| 09.08.1975 | | Stranraer | – | Stenhousemuir | | 0:0 |
| |
Scottish League Cup 1974, Group 9 |
| 10.08.1974 | | Brechin City | – | Stenhousemuir | | 2:2 |
| |
Scottish League Cup 1973, Group 8 |
| 29.08.1973 | | Dunfermline Athletic | – | Stenhousemuir | | 2:2 |
| |
Scottish League Cup 1972, Group 4 |
| 16.08.1972 | | Dunfermline Athletic | – | Stenhousemuir | | 2:2 |
| |
Scottish League Cup 1972, Group 4 |
| 12.08.1972 | | Stenhousemuir | – | Kilmarnock | | 1:1 |
| |
Scottish League Cup 1969, Group 9 |
| 26.08.1969 | | Stenhousemuir | – | Berwick Rangers | | 3:3 |
| |
Scottish League Cup 1969, Group 9 |
| 12.08.1969 | | Stenhousemuir | – | Alloa Athletic | | 3:3 |
| |
Scottish League Cup 1967, Group 9 |
| 26.08.1967 | | East Stirlingshire | – | Stenhousemuir | | 3:3 |
| |
Scottish League Cup 1966, Group 9 |
| 27.08.1966 | | East Stirlingshire | – | Stenhousemuir | | 1:1 |
| |
Scottish League Cup 1966, Group 9 |
| 17.08.1966 | | Stenhousemuir | – | Stranraer | | 1:1 |
| |
Scottish League Cup 1964, Group 6 |
| 15.08.1964 | | Stenhousemuir | – | Stranraer | | 3:3 |
| |
Scottish League Cup 1964, Group 6 |
| 08.08.1964 | | East Stirlingshire Clydebank | – | Stenhousemuir | | 2:2 |
| |
Scottish League Cup 1963, Group 9 |
| 14.08.1963 | | Brechin City | – | Stenhousemuir | | 1:1 |
| |
Scottish League Cup 1963, Group 9 |
| 10.08.1963 | | Stenhousemuir | – | Forfar Athletic | | 2:2 |
| |
Scottish League Cup 1962, Group 9 |
| 15.08.1962 | | Dumbarton | – | Stenhousemuir | | 1:1 |
| |
Scottish League Cup 1960, Group 8 |
| 03.09.1960 | | Stenhousemuir | – | Dundee United | | 1:1 |
| |
Scottish League Cup 1960, Group 8 |
| 31.08.1960 | | Stirling Albion | – | Stenhousemuir | | 2:2 |
| |
Scottish League Cup 1960, Group 8 |
| 20.08.1960 | | Dundee United | – | Stenhousemuir | | 3:3 |
| |
Scottish League Cup 1957, Group 7 |
| 10.08.1957 | | Stenhousemuir | – | Third Lanark | | 3:3 |
| |
Scottish League Cup 1956, Group 8 |
| 18.08.1956 | | Stenhousemuir | – | Ayr United | | 1:1 |
| |
Scottish League Cup 1955, Group 8 |
| 31.08.1955 | | Brechin City | – | Stenhousemuir | | 3:3 |
| |
Scottish League Cup 1955, Group 8 |
| 20.08.1955 | | Stenhousemuir | – | Third Lanark | | 1:1 |
| |
Scottish League Cup 1953, Group 6 |
| 29.08.1953 | | Albion Rovers | – | Stenhousemuir | | 2:2 |
| |
Scottish League Cup 1952, Group 8 |
| 30.08.1952 | | Albion Rovers | – | Stenhousemuir | | 4:4 |
| |
Scottish League Cup 1951, Group 5 |
| 15.08.1951 | | Stenhousemuir | – | Dundee United | | 1:1 |
| |
Scottish League Cup 1950, Group 6 |
| 16.08.1950 | | Stenhousemuir | – | Cowdenbeath | | 2:2 |
| |
Scottish League Cup 1949, Group 5 |
| 27.08.1949 | | Albion Rovers | – | Stenhousemuir | | 2:2 |
| |
Scottish League Cup 1949, Group 5 |
| 20.08.1949 | | Hamilton Academical | – | Stenhousemuir | | 0:0 |
| |
Scottish League Cup 1949, Group 5 |
| 17.08.1949 | | Forfar Athletic | – | Stenhousemuir | | 2:2 |
| |
Scottish League Cup 1948, Group 7 |
| 11.09.1948 | | Stenhousemuir | – | Hamilton Academical | | 1:1 |
| |
Scottish League Cup 1947, Group 7 |
| 09.08.1947 | | Dumbarton | – | Stenhousemuir | | 5:5 |
| |
