First Round
- Aberdeen 3-0 Berwick Rangers
- Ayr United 1-0 Queen of the South
- Dumbarton 0-1 St Mirren
- Dundee 1-2 Heart of Midlothian
- Dundee United 2-1 Queen's Park
- East Stirlingshire 2-0 Stirling Albion
- Falkirk 1-2 Morton
- Kilmarnock 6-0 Glasgow University
- Montrose 1-0 Cowdenbeath
- Motherwell 1-1 Clyde
- Partick Thistle 3-3 Celtic
- Raith Rovers 0-2 Dunfermline Athletic
- Rangers 1-0 Hibernian
- St Johnstone 3-2 Arbroath
- Stenhousemuir 0-3 Airdrieonians
- Stranraer 3-1 East Fife
First Round Replays
- Celtic 8-1 Partick Thistle
Second Round
- Aberdeen 2-2 Dunfermline Athletic
- Airdrieonians 1-1 St Mirren
- Clyde 0-0 Celtic
- Dundee United 6-2 Ayr United
- East Stirlingshire 1-1 St Johnstone
- Montrose 1-1 Kilmarnock
- Rangers 2-0 Heart of Midlothian
- Stranraer 1-3 Morton
Second Round Replays
- Celtic 3-0 Clyde
- Dunfermline Athletic 0-2 Aberdeen
- Kilmarnock 4-1 Montrose
- St Johnstone 3-0 East Stirlingshire
- St Mirren 1-3 Airdrieonians
Quarter Finals
- Aberdeen 0-0 Kilmarnock
- Celtic 3-2 St Johnstone
- Dundee United 2-3 Morton
- Rangers 1-0 Airdrieonians
Quarter Final Replay
Semi-finals
- Celtic 4-1 Morton (@ Hampden Park)
- Rangers 6-1 Aberdeen (@ Celtic)
Final (@ Hampden Park, 26/4/69)
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