| Saturday 5th August 1995 | |||
| First Round | |||
| Albion Rovers | 0-1 | Cowdenbeath | |
| Alloa Athletic | 2-1 | Forfar Athletic | |
| Berwick Rangers | 1-1 | Inverness CT | aet |
| (Berwick Rangers won on penalties) | |||
| Brechin City | 2-3 | East Fife | aet |
| Clyde | 1-2 | East Stirlingshire | |
| Montrose | 0-2 | Livingston | |
| Queen of the South | 3-1 | Queen's Park | |
| Ross County | 0-2 | Arbroath | |
» Scottish League Cup 1995-1996 : Results
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