Scottish League Cup 2019/20, Group B |
 | 27.07.2019 |  | Brechin City | – | Montrose | | 1:1 (0:0),
pen. 2:4 |
| Brechin |
Scottish League Cup 2018/19, Group D |
| 14.07.2018 | | Brechin City | – | Peterhead | | 0:0,
pen. 4:5 |
| Brechin |
Scottish League Cup 2017/18, Group A |
| 18.07.2017 | | Brechin City | – | Forfar Athletic | | 1:1 (0:0),
pen. 4:3 |
| Brechin |
Scottish League Cup 2016/17, First Round, Group B |
| 26.07.2016 | | Brechin City | – | St. Johnstone | | 1:1 (1:0),
pen. 4:2 |
| Brechin |
Scottish League Cup 2010/11, Second Round |
| 24.08.2010 | | Brechin City | – | Dundee | | 2:2 aet
(0:0, 2:2),
pen. 3:1 |
| Brechin |
Scottish League Cup 2005/06, First Round |
| 09.08.2005 | | Brechin City | – | Partick Thistle | | 0:0 aet,
pen. 1:3 |
| |
Scottish League Cup 2004/05, Second Round |
| 24.08.2004 | | Albion Rovers | – | Brechin City | | 1:1 aet
(0:0, 1:1),
pen. 4:3 |
| |
Scottish League Cup 1998, First Round |
| 01.08.1998 | | Brechin City | – | Hamilton Academical | | 2:2 aet,
pen. 2:3 |
| |
Scottish League Cup 1991, Second Round |
| 20.08.1991 | | Brechin City | – | St. Mirren | | 3:3 aet,
pen. 4:5 |
| |
Scottish League Cup 1983/84, Second Round |
| 27.08.1983 | | Celtic | – | Brechin City | | 0:0 |
| |
Scottish League Cup 1982, Group 7 |
| 01.09.1982 | | Brechin City | – | Partick Thistle | | 1:1 |
| |
Scottish League Cup 1982, Group 7 |
| 25.08.1982 | | East Stirlingshire | – | Brechin City | | 1:1 |
| |
Scottish League Cup 1982, Group 7 |
| 21.08.1982 | | Partick Thistle | – | Brechin City | | 0:0 |
| |
Scottish League Cup 1982, Group 7 |
| 14.08.1982 | | East Fife | – | Brechin City | | 0:0 |
| |
Scottish League Cup 1980, Second Round |
| 27.08.1980 | | Brechin City | – | Clyde | | 0:0 |
| |
Scottish League Cup 1977/78, Second Round |
| 03.09.1977 | | Brechin City | – | Queen of the South | | 2:2 |
| |
Scottish League Cup 1976, Group 9 |
| 14.08.1976 | | Meadowbank Thistle | – | Brechin City | | 0:0 |
| |
Scottish League Cup 1975, Group 9 |
| 09.08.1975 | | Brechin City | – | Meadowbank Thistle | | 1:1 |
| |
Scottish League Cup 1974, Group 9 |
| 17.08.1974 | | Brechin City | – | Forfar Athletic | | 1:1 |
| |
Scottish League Cup 1974, Group 9 |
| 10.08.1974 | | Brechin City | – | Stenhousemuir | | 2:2 |
| |
Scottish League Cup 1973, Group 9 |
| 25.08.1973 | | Brechin City | – | Clydebank | | 2:2 |
| |
Scottish League Cup 1971, Group 9 |
| 21.08.1971 | | Alloa Athletic | – | Brechin City | | 1:1 |
| |
Scottish League Cup 1971, Group 9 |
| 18.08.1971 | | Hamilton Academical | – | Brechin City | | 2:2 |
| |
Scottish League Cup 1970, Group 6 |
| 12.08.1970 | | Dumbarton | – | Brechin City | | 2:2 |
| |
Scottish League Cup 1969, Supplementary Round |
| 01.09.1969 | | Brechin City | – | Dumbarton | | 1:1 |
| |
Scottish League Cup 1966, Group 9 |
| 27.08.1966 | | Forfar Athletic | – | Brechin City | | 1:1 |
| |
Scottish League Cup 1963, Group 9 |
| 31.08.1963 | | Forfar Athletic | – | Brechin City | | 3:3 |
| |
Scottish League Cup 1963, Group 9 |
| 24.08.1963 | | Brechin City | – | Montrose | | 2:2 |
| |
Scottish League Cup 1963, Group 9 |
| 14.08.1963 | | Brechin City | – | Stenhousemuir | | 1:1 |
| |
Scottish League Cup 1962, Group 9 |
| 01.09.1962 | | Forfar Athletic | – | Brechin City | | 1:1 |
| |
Scottish League Cup 1959, Group 7 |
| 15.08.1959 | | Queen of the South | – | Brechin City | | 2:2 |
| |
Scottish League Cup 1959, Group 7 |
| 12.08.1959 | | Forfar Athletic | – | Brechin City | | 2:2 |
| |
Scottish League Cup 1959, Group 7 |
| 08.08.1959 | | Brechin City | – | East Fife | | 0:0 |
| |
Scottish League Cup 1957, Group 6 |
| 14.08.1957 | | Cowdenbeath | – | Brechin City | | 1:1 |
| |
Scottish League Cup 1956, Group 5 |
| 18.08.1956 | | Hamilton Academical | – | Brechin City | | 1:1 |
| |
Scottish League Cup 1955, Group 8 |
| 31.08.1955 | | Brechin City | – | Stenhousemuir | | 3:3 |
| |
Scottish League Cup 1954, Group 6 |
| 18.08.1954 | | Ayr United | – | Brechin City | | 2:2 |
| |
Scottish League Cup 1954, Group 6 |
| 14.08.1954 | | Brechin City | – | Dunfermline Athletic | | 1:1 |
| |
