Scottish League Cup 2023/24, Group A |
 | 15.07.2023 | | Stenhousemuir | – | St. Johnstone | | 1:0 (0:0) |
| Stenhousemuir |
Scottish League Cup 2022/23, Group B |
| 19.07.2022 | | Montrose | – | Stenhousemuir | | 0:2 (0:0) |
| Montrose |
Scottish League Cup 2022/23, Group B |
| 16.07.2022 | | Stenhousemuir | – | Fraserburgh | | 3:0 (1:0) |
| Stenhousemuir |
Scottish League Cup 2021/22, Group H |
| 13.07.2021 | | Dumbarton | – | Stenhousemuir | | 1:2 (1:0) |
| Dumbarton |
Scottish League Cup 2019/20, Group A |
| 27.07.2019 | | Stenhousemuir | – | Cowdenbeath | | 2:0 (1:0) |
| Stenhousemuir |
Scottish League Cup 2018/19, Group E |
| 17.07.2018 | | Stenhousemuir | – | Albion Rovers | | 4:0 (0:0) |
| Stenhousemuir |
Scottish League Cup 2014/15, First Round |
| 02.08.2014 | | Airdrieonians | – | Stenhousemuir | | 1:3 (0:2) |
| Airdrie |
Scottish League Cup 2012/13, Second Round |
| 28.08.2012 | | Kilmarnock | – | Stenhousemuir | | 1:2 (0:2) |
| Kilmarnock |
Scottish League Cup 2012/13, First Round |
| 04.08.2012 | | Stenhousemuir | – | Brechin City | | 4:0 (1:0) |
| Stenhousemuir |
Scottish League Cup 2006/07, First Round |
| 08.08.2006 | | Albion Rovers | – | Stenhousemuir | | 1:2 (1:0) |
| Coatbridge |
Scottish League Cup 2004/05, First Round |
| 10.08.2004 | | Stenhousemuir | – | Arbroath | | 2:1 (0:1) |
| |
Scottish League Cup 2000/01, First Round |
| 08.08.2000 | | Stirling Albion | – | Stenhousemuir | | 0:1 |
| |
Scottish League Cup 1998, First Round |
| 01.08.1998 | | Stenhousemuir | – | East Stirlingshire | | 1:0 |
| |
Scottish League Cup 1993, First Round |
| 03.08.1993 | | Stenhousemuir | – | Forfar Athletic | | 3:1 |
| |
Scottish League Cup 1988, First Round |
| 10.08.1988 | | Stenhousemuir | – | Berwick Rangers | | 3:0 |
| |
Scottish League Cup 1986, First Round |
| 13.08.1986 | | Stenhousemuir | – | Queen's Park | | 1:0 |
| |
Scottish League Cup 1978/79, Second Round |
| 30.08.1978 | | Stenhousemuir | – | Clydebank | | 1:0 |
| |
Scottish League Cup 1976, Group 9 |
| 14.08.1976 | | Forfar Athletic | – | Stenhousemuir | | 0:3 |
| |
Scottish League Cup 1975, Group 8 |
| 27.08.1975 | | Stenhousemuir | – | Stranraer | | 3:2 |
| |
Scottish League Cup 1975, Group 8 |
| 23.08.1975 | | Stenhousemuir | – | Morton | | 2:1 |
| |
Scottish League Cup 1975, Group 8 |
| 20.08.1975 | | Albion Rovers | – | Stenhousemuir | | 0:1 |
| |
Scottish League Cup 1974, Group 9 |
| 17.08.1974 | | Stenhousemuir | – | Meadowbank Thistle | | 2:1 |
| |
Scottish League Cup 1974, Group 9 |
| 14.08.1974 | | Stenhousemuir | – | Forfar Athletic | | 3:0 |
| |
Scottish League Cup 1973, Group 8 |
| 11.08.1973 | | Stenhousemuir | – | Dunfermline Athletic | | 1:0 |
| |
Scottish League Cup 1972, Second Round |
| 04.10.1972 | | Rangers | – | Stenhousemuir | | 1:2 |
| |
Scottish League Cup 1972, Group 4 |
| 30.08.1972 | | Stenhousemuir | – | Dundee United | | 2:0 |
| |
Scottish League Cup 1972, Group 4 |
| 23.08.1972 | | Stenhousemuir | – | Dunfermline Athletic | | 5:2 |
| |
Scottish League Cup 1971, Group 6 |
| 28.08.1971 | | Stenhousemuir | – | Queen of the South | | 1:0 |
| |
Scottish League Cup 1971, Group 6 |
| 25.08.1971 | | Dumbarton | – | Stenhousemuir | | 1:2 |
| |
Scottish League Cup 1970, Group 9 |
| 12.08.1970 | | Stenhousemuir | – | Hamilton Academical | | 3:2 |
| |
Scottish League Cup 1968/69, Group 9 |
| 24.08.1968 | | Stenhousemuir | – | Brechin City | | 1:0 |
| |
Scottish League Cup 1968/69, Group 9 |
| 10.08.1968 | | Alloa Athletic | – | Stenhousemuir | | 0:1 |
| |
Scottish League Cup 1967, Group 9 |
| 16.08.1967 | | Stenhousemuir | – | Forfar Athletic | | 3:1 |
| |
Scottish League Cup 1965, Group 9 |
| 04.09.1965 | | Stenhousemuir | – | Brechin City | | 1:0 |
| |
Scottish League Cup 1965, Group 9 |
| 28.08.1965 | | Montrose | – | Stenhousemuir | | 1:3 |
| |
Scottish League Cup 1965, Group 9 |
| 18.08.1965 | | Stenhousemuir | – | Forfar Athletic | | 2:1 |
| |
Scottish League Cup 1963, Group 9 |
| 17.08.1963 | | Montrose | – | Stenhousemuir | | 2:3 |
| |
Scottish League Cup 1962, Group 9 |
| 01.09.1962 | | Albion Rovers | – | Stenhousemuir | | 1:2 |
| |
Scottish League Cup 1962, Group 9 |
| 11.08.1962 | | Stenhousemuir | – | Brechin City | | 2:1 |
| |
Scottish League Cup 1960, Quarterfinal |
| 21.09.1960 | | Stenhousemuir | – | Hamilton Academical | | 5:4 |
| |
Scottish League Cup 1960, Group 8 |
| 27.08.1960 | | Stenhousemuir | – | Brechin City | | 2:1 |
| |
Scottish League Cup 1960, Group 8 |
| 17.08.1960 | | Stenhousemuir | – | Stirling Albion | | 2:0 |
| |
Scottish League Cup 1960, Group 8 |
| 13.08.1960 | | Brechin City | – | Stenhousemuir | | 1:3 |
| |
Scottish League Cup 1959, Group 6 |
| 29.08.1959 | | Dumbarton | – | Stenhousemuir | | 1:2 |
| |
Scottish League Cup 1959, Group 6 |
| 22.08.1959 | | Stenhousemuir | – | Albion Rovers | | 3:0 |
| |
Scottish League Cup 1959, Group 6 |
| 08.08.1959 | | Albion Rovers | – | Stenhousemuir | | 1:2 |
| |
Scottish League Cup 1958, Group 9 |
| 13.08.1958 | | Albion Rovers | – | Stenhousemuir | | 0:4 |
| |
Scottish League Cup 1958, Group 9 |
| 09.08.1958 | | East Stirlingshire | – | Stenhousemuir | | 0:5 |
| |
Scottish League Cup 1957, Group 7 |
| 28.08.1957 | | Stenhousemuir | – | Stirling Albion | | 4:0 |
| |
Scottish League Cup 1957, Group 7 |
| 14.08.1957 | | Stirling Albion | – | Stenhousemuir | | 0:1 |
| |
Scottish League Cup 1956, Group 8 |
| 29.08.1956 | | Dundee United | – | Stenhousemuir | | 3:4 |
| |
Scottish League Cup 1956, Group 8 |
| 25.08.1956 | | Stenhousemuir | – | Third Lanark | | 2:1 |
| |
Scottish League Cup 1956, Group 8 |
| 15.08.1956 | | Stenhousemuir | – | Dundee United | | 3:2 |
| |
Scottish League Cup 1955, Group 8 |
| 17.08.1955 | | Stenhousemuir | – | Brechin City | | 2:0 |
| |
Scottish League Cup 1954, Group 5 |
| 01.09.1954 | | Stenhousemuir | – | Forfar Athletic | | 5:1 |
| |
Scottish League Cup 1954, Group 5 |
| 21.08.1954 | | Stenhousemuir | – | Hamilton Academical | | 4:3 |
| |
Scottish League Cup 1954, Group 5 |
| 18.08.1954 | | Forfar Athletic | – | Stenhousemuir | | 2:3 |
| |
Scottish League Cup 1953, Group 6 |
| 22.08.1953 | | Stenhousemuir | – | Ayr United | | 4:2 |
| |
Scottish League Cup 1953, Group 6 |
| 15.08.1953 | | Stenhousemuir | – | Albion Rovers | | 4:0 |
| |
Scottish League Cup 1953, Group 6 |
| 12.08.1953 | | Stenhousemuir | – | Queen's Park | | 3:2 |
| |
Scottish League Cup 1952, Group 8 |
| 16.08.1952 | | Stenhousemuir | – | Albion Rovers | | 1:0 |
| |
Scottish League Cup 1952, Group 8 |
| 13.08.1952 | | Queen's Park | – | Stenhousemuir | | 1:2 |
| |
Scottish League Cup 1951, Group 5 |
| 01.09.1951 | | Stenhousemuir | – | Cowdenbeath | | 3:1 |
| |
Scottish League Cup 1951, Group 5 |
| 18.08.1951 | | Cowdenbeath | – | Stenhousemuir | | 2:3 |
| |
Scottish League Cup 1950, Group 6 |
| 26.08.1950 | | Stenhousemuir | – | Dundee United | | 3:2 |
| |
Scottish League Cup 1949, Group 5 |
| 03.09.1949 | | Stenhousemuir | – | Hamilton Academical | | 3:0 |
| |
Scottish League Cup 1949, Group 5 |
| 31.08.1949 | | Stenhousemuir | – | Forfar Athletic | | 3:1 |
| |
Scottish League Cup 1948, Group 7 |
| 09.10.1948 | | Stenhousemuir | – | Dundee United | | 2:1 |
| |
Scottish League Cup 1947, Group 7 |
| 06.09.1947 | | St. Johnstone | – | Stenhousemuir | | 0:1 |
| |
Scottish League Cup 1947, Group 7 |
| 30.08.1947 | | Stenhousemuir | – | Dumbarton | | 2:1 |
| |
Scottish League Cup 1947, Group 7 |
| 23.08.1947 | | Stenhousemuir | – | Arbroath | | 2:0 |
| |
Scottish League Cup 1947, Group 7 |
| 16.08.1947 | | Stenhousemuir | – | St. Johnstone | | 3:2 |
| |
Scottish League Cup 1946/47, Section 6 |
| 26.10.1946 | | Raith Rovers | – | Stenhousemuir | | 2:4 |
| |
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