| Tuesday 2nd October 1990 | |||
| First Round | |||
| Airdrieonians | 2-1 | Partick Thistle | aet |
| Alloa Athletic | 3-0 | Forfar Athletic | |
| Arbroath | 2-1 | Queen's Park | aet |
| Ayr United | 3-0 | Brechin City | |
| Clyde | 4-3 | Dumbarton | |
| Clydebank | 1-2 | East Fife | |
| Cowdenbeath | 2-1 | Albion Rovers | |
| Falkirk | 0-3 | Raith Rovers | |
| Kilmarnock | 4-1 | Stirling Albion | |
| Livingston | 1-2 | Morton | aet |
| Montrose | 2-0 | Berwick Rangers | |
| Stenhousemuir | 0-0 | Queen of the South | aet |
| (Stenhousemuir won on penalties) | |||
» Scottish Challenge Cup 1990-1991 : Results
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