Scottish League Cup 2023/24, Group H |
| 22.07.2023 | | Cowdenbeath | | Montrose | | 1:1 (0:0), pen. 4:5 |
| Cowdenbeath |
Scottish League Cup 2021/22, Group C |
| 13.07.2021 | | Forfar Athletic | | Montrose | | 0:0, pen. 5:4 |
| Forfar |
Scottish League Cup 2020/21, Group D |
| 07.10.2020 | | Montrose | | Ross County | | 3:3 (0:2), pen. 4:5 |
| Montrose |
Scottish League Cup 2019/20, Group B |
| 27.07.2019 | | Brechin City | | Montrose | | 1:1 (0:0), pen. 2:4 |
| Brechin |
Scottish League Cup 1994, Second Round |
| 16.08.1994 | | Falkirk | | Montrose | | 1:1 aet, pen. 5:4 |
| |
Scottish League Cup 1994, First Round |
| 09.08.1994 | | Berwick Rangers | | Montrose | | 0:0 aet, pen. 5:4 |
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Scottish League Cup 1982, Group 9 |
| 18.08.1982 | | Stenhousemuir | | Montrose | | 2:2 |
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Scottish League Cup 1979, Second Round |
| 01.09.1979 | | Montrose | | Hibernian | | 1:1 |
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Scottish League Cup 1978/79, Quarterfinal |
| 08.11.1978 | | Montrose | | Celtic | | 1:1 |
| |
Scottish League Cup 1978/79, Second Round |
| 28.08.1978 | | Montrose | | East Stirlingshire | | 1:1 |
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Scottish League Cup 1976, Group 4 |
| 01.09.1976 | | Hibernian | | Montrose | | 0:0 |
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Scottish League Cup 1976, Group 4 |
| 18.08.1976 | | St. Johnstone | | Montrose | | 0:0 |
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Scottish League Cup 1975, Group 6 |
| 23.08.1975 | | East Fife | | Montrose | | 1:1 |
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Scottish League Cup 1975, Group 6 |
| 13.08.1975 | | Montrose | | St. Mirren | | 1:1 |
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Scottish League Cup 1974, Group 6 |
| 28.08.1974 | | Montrose | | Kilmarnock | | 1:1 |
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Scottish League Cup 1974, Group 6 |
| 14.08.1974 | | Montrose | | Queen's Park | | 0:0 |
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Scottish League Cup 1973, Group 7 |
| 18.08.1973 | | Montrose | | Airdrieonians | | 2:2 |
| |
Scottish League Cup 1973, Group 7 |
| 11.08.1973 | | Montrose | | Clyde | | 2:2 |
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Scottish League Cup 1971, Group 8 |
| 21.08.1971 | | Montrose | | Stranraer | | 2:2 |
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Scottish League Cup 1971, Group 8 |
| 18.08.1971 | | Montrose | | Albion Rovers | | 1:1 |
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Scottish League Cup 1969, Group 5 |
| 23.08.1969 | | Montrose | | Albion Rovers | | 1:1 |
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Scottish League Cup 1966, Quarterfinal |
| 14.09.1966 | | Montrose | | Airdrieonians | | 3:3 |
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Scottish League Cup 1966, Group 8 |
| 03.09.1966 | | Montrose | | Albion Rovers | | 2:2 |
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Scottish League Cup 1966, Group 8 |
| 20.08.1966 | | Albion Rovers | | Montrose | | 0:0 |
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Scottish League Cup 1963, Group 9 |
| 24.08.1963 | | Brechin City | | Montrose | | 2:2 |
| |
Scottish League Cup 1962, Group 7 |
| 01.09.1962 | | Montrose | | Queen of the South | | 0:0 |
| |
Scottish League Cup 1962, Group 7 |
| 25.08.1962 | | Queen's Park | | Montrose | | 1:1 |
| |
Scottish League Cup 1961, Group 6 |
| 12.08.1961 | | Montrose | | Hamilton Academical | | 2:2 |
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Scottish League Cup 1959, Group 9 |
| 12.08.1959 | | Montrose | | Dundee United | | 1:1 |
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Scottish League Cup 1958, Group 8 |
| 09.08.1958 | | Montrose | | Forfar Athletic | | 2:2 |
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