Scottish League Cup 2016/17, First Round, Group F |
 | 30.07.2016 |  | East Stirlingshire | – | Annan Athletic | | 0:2 (0:0) |
| Stenhousemuir |
Scottish League Cup 2016/17, First Round, Group F |
| 26.07.2016 | | Motherwell | – | East Stirlingshire | | 3:0 (0:0) |
| Motherwell |
Scottish League Cup 2016/17, First Round, Group F |
| 22.07.2016 | | East Stirlingshire | – | Rangers | | 0:3 (0:2) |
| Stenhousemuir |
Scottish League Cup 2016/17, First Round, Group F |
| 19.07.2016 | | Stranraer | – | East Stirlingshire | | 3:1 (0:0) |
| Stranraer |
Scottish League Cup 2015/16, First Round |
| 31.07.2015 | | Falkirk | – | East Stirlingshire | | 5:0 (1:0) |
| Cumbernauld |
Scottish League Cup 2014/15, First Round |
| 02.08.2014 | | East Stirlingshire | – | Ayr United | | 0:4 (0:0) |
| Stenhousemuir |
Scottish League Cup 2013/14, First Round |
| 03.08.2013 | | East Stirlingshire | – | Dunfermline Athletic | | 0:2 (0:1) |
| Stenhousemuir |
Scottish League Cup 2012/13, First Round |
| 05.08.2012 | | East Stirlingshire | – | Greenock Morton | | 1:5 (1:3) |
| Stenhousemuir |
Scottish League Cup 2011/12, First Round |
| 30.07.2011 | | East Stirlingshire | – | Ayr United | | 0:3 |
| Stenhousemuir |
Scottish League Cup 2010/11, First Round |
| 01.08.2010 | | East Stirlingshire | – | Alloa Athletic | | 1:2 (1:1) |
| Stenhousemuir |
Scottish League Cup 2009/10, First Round |
| 02.08.2009 | | East Stirlingshire | – | St. Mirren | | 3:6 (3:4) |
| Stenhousemuir |
Scottish League Cup 2008/09, First Round |
| 06.08.2008 | | East Stirlingshire | – | Livingston | | 1:2 aet
(0:0, 1:1) |
| Stenhousemuir |
Scottish League Cup 2007/08, First Round |
| 07.08.2007 | | Hamilton Academical | – | East Stirlingshire | | 2:1 (1:0) |
| Hamilton |
Scottish League Cup 2006/07, First Round |
| 08.08.2006 | | Cowdenbeath | – | East Stirlingshire | | 4:1 (4:0) |
| Cowdenbeath |
Scottish League Cup 2005/06, First Round |
| 09.08.2005 | | East Stirlingshire | – | Queen's Park | | 1:3 (0:3) |
| |
Scottish League Cup 2004/05, First Round |
| 10.08.2004 | | Peterhead | – | East Stirlingshire | | 3:2 (1:0) |
| |
Scottish League Cup 2003/04, First Round |
| 02.09.2003 | | East Stirlingshire | – | Ross County | | 1:2 (0:0) |
| |
Scottish League Cup 2002/03, First Round |
| 07.09.2002 | | Queen's Park | – | East Stirlingshire | | 1:0 (0:0) |
| |
Scottish League Cup 2001/02, First Round |
| 11.09.2001 | | East Stirlingshire | – | Queen of the South | | 0:3 |
| |
Scottish League Cup 2000/01, Second Round |
| 22.08.2000 | | Dunfermline Athletic | – | East Stirlingshire | | 1:0 |
| |
Scottish League Cup 1999/00, Second Round |
| 18.08.1999 | | East Stirlingshire | – | Falkirk | | 0:2 aet
(0:0) |
| |
Scottish League Cup 1998, First Round |
| 01.08.1998 | | Stenhousemuir | – | East Stirlingshire | | 1:0 |
| |
Scottish League Cup 1997, Second Round |
| 09.08.1997 | | Dundee | – | East Stirlingshire | | 1:0 |
| |
Scottish League Cup 1996, First Round |
| 03.08.1996 | | East Stirlingshire | – | Alloa Athletic | | 1:3 |
| |
Scottish League Cup 1995, Second Round |
| 19.08.1995 | | East Stirlingshire | – | Dundee | | 0:6 |
| |
Scottish League Cup 1994, First Round |
| 09.08.1994 | | East Stirlingshire | – | Inverness | | 0:2 |
| |
Scottish League Cup 1993, Second Round |
| 11.08.1993 | | Dunfermline Athletic | – | East Stirlingshire | | 2:0 |
| |
Scottish League Cup 1992, First Round |
| 01.08.1992 | | East Stirlingshire | – | Alloa Athletic | | 0:1 |
| |
Scottish League Cup 1991, Second Round |
| 20.08.1991 | | Falkirk | – | East Stirlingshire | | 3:0 |
| |
Scottish League Cup 1990, Second Round |
| 21.08.1990 | | Rangers | – | East Stirlingshire | | 5:0 |
| |
Scottish League Cup 1989, First Round |
| 09.08.1989 | | Arbroath | – | East Stirlingshire | | 1:0 |
| |
Scottish League Cup 1988, First Round |
| 11.08.1988 | | East Stirlingshire | – | Arbroath | | 0:1 |
| |
Scottish League Cup 1987, Second Round |
| 18.08.1987 | | East Stirlingshire | – | Dunfermline Athletic | | 1:3 |
| |
Scottish League Cup 1986, Second Round |
| 20.08.1986 | | Hibernian | – | East Stirlingshire | | 1:0 |
| |
Scottish League Cup 1985, First Round |
| 14.08.1985 | | East Stirlingshire | – | Raith Rovers | | 1:3 |
| |
Scottish League Cup 1984, Second Round |
| 21.08.1984 | | Hearts | – | East Stirlingshire | | 4:0 |
| |
Scottish League Cup 1983/84, First Round |
| 17.08.1983 | | East Stirlingshire | – | Montrose | | 1:2 |
| |
Scottish League Cup 1983/84, First Round |
| 13.08.1983 | | Montrose | – | East Stirlingshire | | 1:0 |
| |
Scottish League Cup 1982, Group 7 |
| 28.08.1982 | | Partick Thistle | – | East Stirlingshire | | 4:2 |
| |
Scottish League Cup 1982, Group 7 |
| 18.08.1982 | | Brechin City | – | East Stirlingshire | | 4:0 |
| |
Scottish League Cup 1982, Group 7 |
| 14.08.1982 | | East Stirlingshire | – | Partick Thistle | | 0:4 |
| |
Scottish League Cup 1981, Group 8 |
| 26.08.1981 | | East Stirlingshire | – | Dunfermline Athletic | | 0:1 |
| |
Scottish League Cup 1981, Group 8 |
| 22.08.1981 | | East Stirlingshire | – | Montrose | | 1:2 |
| |
Scottish League Cup 1981, Group 8 |
| 19.08.1981 | | Hamilton Academical | – | East Stirlingshire | | 1:0 |
| |
Scottish League Cup 1981, Group 8 |
| 15.08.1981 | | Dunfermline Athletic | – | East Stirlingshire | | 2:1 |
| |
Scottish League Cup 1981, Group 8 |
| 12.08.1981 | | East Stirlingshire | – | Hamilton Academical | | 0:2 |
| |
Scottish League Cup 1981, Group 8 |
| 08.08.1981 | | Montrose | – | East Stirlingshire | | 1:0 |
| |
Scottish League Cup 1980, First Round |
| 19.08.1980 | | East Stirlingshire | – | Queen's Park | | 0:4 |
| |
Scottish League Cup 1980, First Round |
| 13.08.1980 | | Queen's Park | – | East Stirlingshire | | 1:0 |
| |
Scottish League Cup 1979, First Round |
| 27.08.1979 | | Albion Rovers | – | East Stirlingshire | | 4:1 |
| |
Scottish League Cup 1978/79, Second Round |
| 02.09.1978 | | East Stirlingshire | – | Montrose | | 0:2 aet |
| |
Scottish League Cup 1977/78, Second Round |
| 31.08.1977 | | East Stirlingshire | – | Stirling Albion | | 0:1 |
| |
Scottish League Cup 1976, Group 7 |
| 28.08.1976 | | East Stirlingshire | – | Stirling Albion | | 0:6 |
| |
Scottish League Cup 1976, Group 7 |
| 14.08.1976 | | Cowdenbeath | – | East Stirlingshire | | 2:1 |
| |
Scottish League Cup 1975, Group 7 |
| 23.08.1975 | | East Stirlingshire | – | Clydebank | | 0:1 |
| |
Scottish League Cup 1975, Group 7 |
| 20.08.1975 | | Arbroath | – | East Stirlingshire | | 3:1 |
| |
Scottish League Cup 1975, Group 7 |
| 13.08.1975 | | East Stirlingshire | – | Arbroath | | 0:4 |
| |
Scottish League Cup 1974, Group 9 |
| 17.08.1974 | | East Stirlingshire | – | Albion Rovers | | 1:2 |
| |
Scottish League Cup 1973, Supplementary Round |
| 03.09.1973 | | Albion Rovers | – | East Stirlingshire | | 1:0 |
| |
Scottish League Cup 1973, Group 5 |
| 29.08.1973 | | Kilmarnock | – | East Stirlingshire | | 4:0 |
| |
Scottish League Cup 1973, Group 5 |
| 22.08.1973 | | East Stirlingshire | – | Queen's Park | | 1:3 |
| |
Scottish League Cup 1972, Group 7 |
| 30.08.1972 | | East Stirlingshire | – | Clyde | | 0:2 |
| |
Scottish League Cup 1972, Group 7 |
| 26.08.1972 | | Dundee | – | East Stirlingshire | | 3:0 |
| |
Scottish League Cup 1972, Group 7 |
| 23.08.1972 | | East Stirlingshire | – | Motherwell | | 1:5 |
| |
Scottish League Cup 1972, Group 7 |
| 19.08.1972 | | Clyde | – | East Stirlingshire | | 3:1 |
| |
Scottish League Cup 1972, Group 7 |
| 16.08.1972 | | Motherwell | – | East Stirlingshire | | 1:0 |
| |
Scottish League Cup 1972, Group 7 |
| 12.08.1972 | | East Stirlingshire | – | Dundee | | 2:8 |
| |
Scottish League Cup 1971, Group 9 |
| 28.08.1971 | | East Stirlingshire | – | Hamilton Academical | | 2:6 |
| |
Scottish League Cup 1970, Group 7 |
| 26.08.1970 | | Montrose | – | East Stirlingshire | | 2:1 |
| |
Scottish League Cup 1970, Group 7 |
| 22.08.1970 | | East Stirlingshire | – | Cowdenbeath | | 1:4 |
| |
Scottish League Cup 1970, Group 7 |
| 19.08.1970 | | Raith Rovers | – | East Stirlingshire | | 2:1 |
| |
Scottish League Cup 1970, Group 7 |
| 15.08.1970 | | East Stirlingshire | – | Montrose | | 1:2 |
| |
Scottish League Cup 1969, Group 6 |
| 16.08.1969 | | Queen's Park | – | East Stirlingshire | | 7:2 |
| |
Scottish League Cup 1969, Group 6 |
| 13.08.1969 | | East Stirlingshire | – | Ayr United | | 0:1 |
| |
Scottish League Cup 1969, Group 6 |
| 09.08.1969 | | Queen of the South | – | East Stirlingshire | | 2:0 |
| |
Scottish League Cup 1968/69, Group 9 |
| 31.08.1968 | | Brechin City | – | East Stirlingshire | | 3:0 |
| |
Scottish League Cup 1968/69, Group 9 |
| 10.08.1968 | | Stranraer | – | East Stirlingshire | | 2:1 |
| |
Scottish League Cup 1967, Group 9 |
| 19.08.1967 | | Brechin City | – | East Stirlingshire | | 2:1 |
| |
Scottish League Cup 1967, Group 9 |
| 16.08.1967 | | East Stirlingshire | – | Clydebank | | 0:1 |
| |
Scottish League Cup 1967, Group 9 |
| 12.08.1967 | | Forfar Athletic | – | East Stirlingshire | | 4:0 |
| |
Scottish League Cup 1966, Group 9 |
| 03.09.1966 | | Forfar Athletic | – | East Stirlingshire | | 5:1 |
| |
Scottish League Cup 1966, Group 9 |
| 17.08.1966 | | East Stirlingshire | – | Brechin City | | 0:4 |
| |
Scottish League Cup 1966, Group 9 |
| 13.08.1966 | | Clydebank | – | East Stirlingshire | | 3:0 |
| |
Scottish League Cup 1965, Group 8 |
| 01.09.1965 | | Alloa Athletic | – | East Stirlingshire Clydebank | | 2:1 |
| |
Scottish League Cup 1965, Group 8 |
| 21.08.1965 | | East Fife | – | East Stirlingshire Clydebank | | 4:1 |
| |
Scottish League Cup 1965, Group 8 |
| 14.08.1965 | | Dumbarton | – | East Stirlingshire Clydebank | | 2:1 |
| |
Scottish League Cup 1964, Group 6 |
| 15.08.1964 | | East Stirlingshire Clydebank | – | Hamilton Academical | | 2:4 |
| |
Scottish League Cup 1963, Group 7 |
| 14.08.1963 | | St. Johnstone | – | East Stirlingshire | | 3:1 |
| |
Scottish League Cup 1962, Group 5 |
| 01.09.1962 | | Berwick Rangers | – | East Stirlingshire | | 2:0 |
| |
Scottish League Cup 1962, Group 5 |
| 29.08.1962 | | East Stirlingshire | – | Hamilton Academical | | 0:1 |
| |
Scottish League Cup 1962, Group 5 |
| 25.08.1962 | | Ayr United | – | East Stirlingshire | | 2:1 |
| |
Scottish League Cup 1961, Group 9 |
| 02.09.1961 | | Queen's Park | – | East Stirlingshire | | 7:2 |
| |
Scottish League Cup 1961, Group 9 |
| 12.08.1961 | | Albion Rovers | – | East Stirlingshire | | 5:2 |
| |
Scottish League Cup 1960, Group 9 |
| 20.08.1960 | | Cowdenbeath | – | East Stirlingshire | | 3:0 |
| |
Scottish League Cup 1960, Group 9 |
| 17.08.1960 | | East Stirlingshire | – | Stranraer | | 1:3 |
| |
Scottish League Cup 1959, Group 9 |
| 22.08.1959 | | Stranraer | – | East Stirlingshire | | 2:1 |
| |
Scottish League Cup 1959, Group 9 |
| 12.08.1959 | | East Stirlingshire | – | Queen's Park | | 1:2 |
| |
Scottish League Cup 1959, Group 9 |
| 08.08.1959 | | Dundee United | – | East Stirlingshire | | 2:0 |
| |
Scottish League Cup 1958, Group 9 |
| 23.08.1958 | | Albion Rovers | – | East Stirlingshire | | 4:1 |
| |
Scottish League Cup 1958, Group 9 |
| 16.08.1958 | | East Stirlingshire | – | Stranraer | | 1:2 |
| |
Scottish League Cup 1958, Group 9 |
| 13.08.1958 | | Berwick Rangers | – | East Stirlingshire | | 3:2 |
| |
Scottish League Cup 1958, Group 9 |
| 09.08.1958 | | East Stirlingshire | – | Stenhousemuir | | 0:5 |
| |
Scottish League Cup 1957, Group 9 |
| 17.08.1957 | | Forfar Athletic | – | East Stirlingshire | | 2:1 |
| |
Scottish League Cup 1956, Group 9 |
| 25.08.1956 | | East Stirlingshire | – | Arbroath | | 0:3 |
| |
Scottish League Cup 1956, Group 9 |
| 18.08.1956 | | Albion Rovers | – | East Stirlingshire | | 9:2 |
| |
Scottish League Cup 1955, Group 9 |
| 03.09.1955 | | Dumbarton | – | East Stirlingshire | | 6:1 |
| |
Scottish League Cup 1948, Group 6 |
| 09.10.1948 | | East Stirlingshire | – | Alloa Athletic | | 1:3 |
| |
Scottish League Cup 1948, Group 6 |
| 02.10.1948 | | Kilmarnock | – | East Stirlingshire | | 4:1 |
| |
Scottish League Cup 1948, Group 6 |
| 25.09.1948 | | Queen's Park | – | East Stirlingshire | | 2:0 |
| |
Scottish League Cup 1948, Group 6 |
| 18.09.1948 | | Alloa Athletic | – | East Stirlingshire | | 1:0 |
| |
