Scottish League Cup 2023/24, Group C |
 | 25.07.2023 |  | Clyde | – | Brechin City | | 1:2 (0:1) |
| Cumbernauld |
Scottish League Cup 2021/22, Group D |
| 20.07.2021 | | Brechin City | – | Alloa Athletic | | 1:0 (0:0) |
| Brechin |
Scottish League Cup 2018/19, Group D |
| 17.07.2018 | | Stirling Albion | – | Brechin City | | 1:2 (1:1) |
| Stirling |
Scottish League Cup 2016/17, First Round, Group B |
| 19.07.2016 | | Brechin City | – | Stirling Albion | | 2:1 (1:1) |
| Brechin |
Scottish League Cup 2010/11, First Round |
| 31.07.2010 | | Stenhousemuir | – | Brechin City | | 1:3 (1:2) |
| Stenhousemuir |
Scottish League Cup 2009/10, First Round |
| 01.08.2009 | | Brechin City | – | Elgin City | | 4:0 (1:0) |
| Brechin |
Scottish League Cup 2008/09, First Round |
| 06.08.2008 | | East Fife | – | Brechin City | | 0:3 (0:1) |
| Methil |
Scottish League Cup 2006/07, First Round |
| 08.08.2006 | | Brechin City | – | Greenock Morton | | 2:1 (0:1) |
| Brechin |
Scottish League Cup 2004/05, First Round |
| 10.08.2004 | | Brechin City | – | Cowdenbeath | | 5:2 aet
(1:1, 2:2) |
| |
Scottish League Cup 2003/04, Second Round |
| 23.09.2003 | | Brechin City | – | Kilmarnock | | 1:0 (1:0) |
| |
Scottish League Cup 2003/04, First Round |
| 02.09.2003 | | Elgin City | – | Brechin City | | 0:4 (0:1) |
| |
Scottish League Cup 1996, First Round |
| 03.08.1996 | | Brechin City | – | Montrose | | 3:0 |
| |
Scottish League Cup 1992, Second Round |
| 11.08.1992 | | Brechin City | – | Hamilton Academical | | 4:2 |
| |
Scottish League Cup 1992, First Round |
| 04.08.1992 | | Brechin City | – | Albion Rovers | | 2:1 |
| |
Scottish League Cup 1989, First Round |
| 09.08.1989 | | Stranraer | – | Brechin City | | 3:4 aet |
| |
Scottish League Cup 1988, First Round |
| 10.08.1988 | | Brechin City | – | Montrose | | 3:1 |
| |
Scottish League Cup 1985, Second Round |
| 21.08.1985 | | Brechin City | – | Falkirk | | 3:1 |
| |
Scottish League Cup 1984, Second Round |
| 21.08.1984 | | Stirling Albion | – | Brechin City | | 1:4 |
| |
Scottish League Cup 1982, Group 7 |
| 28.08.1982 | | Brechin City | – | East Fife | | 4:0 |
| |
Scottish League Cup 1982, Group 7 |
| 18.08.1982 | | Brechin City | – | East Stirlingshire | | 4:0 |
| |
Scottish League Cup 1981, Group 5 |
| 26.08.1981 | | Dumbarton | – | Brechin City | | 1:3 |
| |
Scottish League Cup 1981, Group 5 |
| 15.08.1981 | | Brechin City | – | Dumbarton | | 2:1 |
| |
Scottish League Cup 1981, Group 5 |
| 12.08.1981 | | Brechin City | – | Cowdenbeath | | 2:0 |
| |
Scottish League Cup 1981, Group 5 |
| 08.08.1981 | | Queen of the South | – | Brechin City | | 1:3 |
| |
Scottish League Cup 1976, Group 9 |
| 25.08.1976 | | Forfar Athletic | – | Brechin City | | 0:2 |
| |
Scottish League Cup 1976, Group 9 |
| 21.08.1976 | | Brechin City | – | Stenhousemuir | | 2:0 |
| |
Scottish League Cup 1976, Group 9 |
| 18.08.1976 | | Brechin City | – | Berwick Rangers | | 3:1 |
| |
Scottish League Cup 1975, Group 9 |
| 27.08.1975 | | Queen's Park | – | Brechin City | | 1:2 |
| |
Scottish League Cup 1975, Group 9 |
| 23.08.1975 | | Brechin City | – | Alloa Athletic | | 2:1 |
| |
Scottish League Cup 1974, Group 9 |
| 28.08.1974 | | Meadowbank Thistle | – | Brechin City | | 1:4 |
| |
Scottish League Cup 1973, Group 9 |
| 15.08.1973 | | Brechin City | – | Forfar Athletic | | 1:0 |
| |
Scottish League Cup 1972, Group 9 |
| 16.08.1972 | | Brechin City | – | Forfar Athletic | | 2:1 |
| |
Scottish League Cup 1971, Group 9 |
| 28.08.1971 | | Brechin City | – | Forfar Athletic | | 2:1 |
| |
Scottish League Cup 1969, Group 9 |
| 16.08.1969 | | Brechin City | – | Stenhousemuir | | 2:1 |
| |
Scottish League Cup 1969, Group 9 |
| 13.08.1969 | | Hamilton Academical | – | Brechin City | | 1:2 |
| |
Scottish League Cup 1969, Group 9 |
| 09.08.1969 | | Brechin City | – | Berwick Rangers | | 1:0 |
| |
Scottish League Cup 1968/69, Group 9 |
| 31.08.1968 | | Brechin City | – | East Stirlingshire | | 3:0 |
| |
Scottish League Cup 1968/69, Group 9 |
| 17.08.1968 | | Stranraer | – | Brechin City | | 1:2 |
| |
Scottish League Cup 1967, Group 9 |
| 02.09.1967 | | Stenhousemuir | – | Brechin City | | 2:4 |
| |
Scottish League Cup 1967, Group 9 |
| 26.08.1967 | | Brechin City | – | Forfar Athletic | | 2:1 |
| |
Scottish League Cup 1967, Group 9 |
| 19.08.1967 | | Brechin City | – | East Stirlingshire | | 2:1 |
| |
Scottish League Cup 1966, Group 9 |
| 03.09.1966 | | Stranraer | – | Brechin City | | 1:2 |
| |
Scottish League Cup 1966, Group 9 |
| 20.08.1966 | | Brechin City | – | Clydebank | | 3:1 |
| |
Scottish League Cup 1966, Group 9 |
| 17.08.1966 | | East Stirlingshire | – | Brechin City | | 0:4 |
| |
Scottish League Cup 1966, Group 9 |
| 13.08.1966 | | Brechin City | – | Stenhousemuir | | 4:0 |
| |
Scottish League Cup 1965, Group 9 |
| 21.08.1965 | | Brechin City | – | Forfar Athletic | | 1:0 |
| |
Scottish League Cup 1964, Group 9 |
| 29.08.1964 | | Cowdenbeath | – | Brechin City | | 2:3 |
| |
Scottish League Cup 1960, Group 8 |
| 31.08.1960 | | Brechin City | – | Dundee United | | 2:1 |
| |
Scottish League Cup 1959, Group 7 |
| 29.08.1959 | | Brechin City | – | Queen of the South | | 2:1 |
| |
Scottish League Cup 1959, Group 7 |
| 26.08.1959 | | Brechin City | – | Forfar Athletic | | 6:1 |
| |
Scottish League Cup 1957, Quarterfinal |
| 14.09.1957 | | Brechin City | – | Hamilton Academical | | 1:0 |
| |
Scottish League Cup 1957, Quarterfinal |
| 11.09.1957 | | Hamilton Academical | – | Brechin City | | 2:4 |
| |
Scottish League Cup 1957, Group 6 |
| 28.08.1957 | | Brechin City | – | Cowdenbeath | | 7:1 |
| |
Scottish League Cup 1957, Group 6 |
| 17.08.1957 | | Brechin City | – | Dunfermline Athletic | | 2:1 |
| |
Scottish League Cup 1957, Group 6 |
| 10.08.1957 | | Brechin City | – | Ayr United | | 5:2 |
| |
Scottish League Cup 1956, Quarterfinal |
| 12.09.1956 | | Brechin City | – | Clyde | | 3:2 |
| |
Scottish League Cup 1956, Group 5 |
| 01.09.1956 | | Brechin City | – | Hamilton Academical | | 2:0 |
| |
Scottish League Cup 1956, Group 5 |
| 29.08.1956 | | Alloa Athletic | – | Brechin City | | 1:3 |
| |
Scottish League Cup 1956, Group 5 |
| 15.08.1956 | | Brechin City | – | Alloa Athletic | | 3:1 |
| |
Scottish League Cup 1956, Group 5 |
| 11.08.1956 | | Dumbarton | – | Brechin City | | 1:8 |
| |
Scottish League Cup 1955, Group 8 |
| 03.09.1955 | | Brechin City | – | Morton | | 4:0 |
| |
Scottish League Cup 1955, Group 8 |
| 27.08.1955 | | Third Lanark | – | Brechin City | | 1:4 |
| |
Scottish League Cup 1955, Group 8 |
| 13.08.1955 | | Brechin City | – | Third Lanark | | 2:1 |
| |
Scottish League Cup 1954, Group 6 |
| 04.09.1954 | | Dundee United | – | Brechin City | | 0:1 |
| |
Scottish League Cup 1954, Group 6 |
| 21.08.1954 | | Brechin City | – | Dundee United | | 2:0 |
| |
