Scottish League Cup 1991, First Round |
 | 13.08.1991 |  | East Fife | – | East Stirlingshire | | 2:2 aet,
pen. 2:4 |
| |
Scottish League Cup 1990, First Round |
| 14.08.1990 | | East Stirlingshire | – | Dumbarton | | 2:2 aet,
pen. 4:1 |
| |
Scottish League Cup 1984, First Round |
| 15.08.1984 | | East Stirlingshire | – | Berwick Rangers | | 1:1 aet,
pen. 4:3 |
| |
Scottish League Cup 1982, Group 7 |
| 01.09.1982 | | East Stirlingshire | – | East Fife | | 0:0 |
| |
Scottish League Cup 1982, Group 7 |
| 25.08.1982 | | East Stirlingshire | – | Brechin City | | 1:1 |
| |
Scottish League Cup 1979, First Round |
| 15.08.1979 | | East Stirlingshire | – | Albion Rovers | | 1:1 |
| |
Scottish League Cup 1978/79, Second Round |
| 28.08.1978 | | Montrose | – | East Stirlingshire | | 1:1 |
| |
Scottish League Cup 1977/78, Second Round |
| 03.09.1977 | | Stirling Albion | – | East Stirlingshire | | 0:0 |
| |
Scottish League Cup 1976, Group 7 |
| 25.08.1976 | | Morton | – | East Stirlingshire | | 1:1 |
| |
Scottish League Cup 1976, Group 7 |
| 21.08.1976 | | Stirling Albion | – | East Stirlingshire | | 1:1 |
| |
Scottish League Cup 1976, Group 7 |
| 18.08.1976 | | East Stirlingshire | – | Morton | | 1:1 |
| |
Scottish League Cup 1975, Group 7 |
| 27.08.1975 | | East Stirlingshire | – | Berwick Rangers | | 2:2 |
| |
Scottish League Cup 1975, Group 7 |
| 16.08.1975 | | Clydebank | – | East Stirlingshire | | 1:1 |
| |
Scottish League Cup 1974, Group 9 |
| 10.08.1974 | | Forfar Athletic | – | East Stirlingshire | | 3:3 |
| |
Scottish League Cup 1973, Supplementary Round |
| 05.09.1973 | | East Stirlingshire | – | Albion Rovers | | 0:0 |
| |
Scottish League Cup 1973, Group 5 |
| 25.08.1973 | | Hamilton Academical | – | East Stirlingshire | | 0:0 |
| |
Scottish League Cup 1971, Group 9 |
| 18.08.1971 | | East Stirlingshire | – | Alloa Athletic | | 1:1 |
| |
Scottish League Cup 1971, Group 9 |
| 14.08.1971 | | Forfar Athletic | – | East Stirlingshire | | 2:2 |
| |
Scottish League Cup 1970, Group 7 |
| 08.08.1970 | | Cowdenbeath | – | East Stirlingshire | | 1:1 |
| |
Scottish League Cup 1969, Group 6 |
| 27.08.1969 | | East Stirlingshire | – | Queen's Park | | 0:0 |
| |
Scottish League Cup 1969, Group 6 |
| 20.08.1969 | | Ayr United | – | East Stirlingshire | | 0:0 |
| |
Scottish League Cup 1968/69, Group 9 |
| 24.08.1968 | | East Stirlingshire | – | Alloa Athletic | | 2:2 |
| |
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 |
| 20.08.1966 | | East Stirlingshire | – | Stranraer | | 0:0 |
| |
Scottish League Cup 1964, Group 6 |
| 29.08.1964 | | Hamilton Academical | – | East Stirlingshire Clydebank | | 0:0 |
| |
Scottish League Cup 1964, Group 6 |
| 26.08.1964 | | East Stirlingshire Clydebank | – | Stranraer | | 3:3 |
| |
Scottish League Cup 1964, Group 6 |
| 12.08.1964 | | Stranraer | – | East Stirlingshire Clydebank | | 2:2 |
| |
Scottish League Cup 1964, Group 6 |
| 08.08.1964 | | East Stirlingshire Clydebank | – | Stenhousemuir | | 2:2 |
| |
Scottish League Cup 1962, Group 5 |
| 15.08.1962 | | Hamilton Academical | – | East Stirlingshire | | 4:4 |
| |
Scottish League Cup 1960, Group 9 |
| 13.08.1960 | | Forfar Athletic | – | East Stirlingshire | | 2:2 |
| |
Scottish League Cup 1957, Group 9 |
| 14.08.1957 | | Alloa Athletic | – | East Stirlingshire | | 3:3 |
| |
Scottish League Cup 1948, Group 6 |
| 16.10.1948 | | East Stirlingshire | – | Queen's Park | | 1:1 |
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