1st Round (28th January, 1950):
| Alloa 0-1 Albion Rovers |
| Brechin City 0-3 Celtic |
| Clachnaccudin 2-3 Stenh'semuir |
| Clyde 4-3 Newton S |
| Cowdenbeath 1-0 Hamilton Academicals |
| Dumbarton 1-0 Queen's Park |
| Dundee Utd 4-0 Ayr |
| Dunfermline 5-3 Forfar |
| East Fife 4-0 Fraserburgh |
| Hearts 1-1 Dundee |
| Hibernian 0-1 Partick Thistle |
| Inverness Caledonian 0-1 Queen of the South |
| Kilmarnock 1-1 Stirling Albion |
| Motherwell 2-4 Rangers |
| Raith Rovers 3-0 Airdrie |
| Ross County 0-3 Morton |
| St Johnstone 7-3 Leith Athletic |
| St Mirren 1-2 Aberdeen |
| Stranraer 1-3 Falkirk |
| Third Lanark 2-1 Arbroath |
Replays 1st Round (1st & 6th February, 1950)
| Dundee 1-2 Hearts |
| Stirling Albion 3-1 Kilmarnock
2nd Round (11th – 22nd February, 1950)
| Aberdeen 3-1 Hearts |
| Falkirk 2-3 East Fife |
| Queen of the South 1-1 Morton |
| Raith Rovers 3-2 Clyde |
| Rangers 8-0 Cowdenbeath |
| Stenh'semuir 2-2 St Johnstone |
| Stirling Albion 2-2 Dumbarton |
| Partick Thistle 5-0 Dundee Utd |
| Albion Rovers 1-2 Dunfermline |
| Third Lanark 1-1 Celtic |
| Stirling 6-2 Dumbarton
Replays 2nd Round (15th – 20th February, 1950)
| Morton 0-3 Queen of the South |
| St Johnstone 2-4 Stenh'semuir |
| Dumbarton 1-1 Stirling Albion |
| Celtic 4-1 Third Lanark
3rd Round (25th February, 1950)
| Celtic 0-1 Aberdeen |
Dunfermline 1-4 Stenh'semuir
Bye: 6 Clubs
Quarter Finals (11th March, 1950)
| Partick Thistle 5-1 Stirling Albion |
| Queen of the South 3-3 Aberdeen |
| Rangers 1-1 Raith Rovers |
| Stenh'semuir 0-3 East Fife
Replays Quarter Finals (15th and 27th March, 1950)
| Raith Rovers 1-1 Rangers |
| Aberdeen 1-2 Queen of the South |
| Rangers 2-0 Raith
Semi Finals (1st April, 1950)
| Partick Thistle 1-2 East Fife |
| Queen of the South 1-1 Rangers
Replay Semi Final (5th April, 1950)
| Rangers 3-0 Queen of the South
Final (Hampden Park 22nd April, 1950)
| Rangers 3-0 East Fife
Cup Winners 1950: Rangers |
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