| Saturday 21st January 1939 | |||
| First Round | |||
| Aberdeen | 1-0 | Albion Rovers | |
| Alloa Athletic | 2-1 | Ayr United | |
| Blairgowrie | 3-2 | Dumbarton | |
| Bo'ness | 1-4 | Hamilton Academical | |
| Burntisland Shipyard | 3-8 | Celtic | |
| Clyde | 2-0 | St Johnstone | |
| Cowdenbeath | 3-3 | Partick Thistle | |
| Dundee | 2-0 | St Bernard's | |
| Dundee United | 2-0 | Stenhousemuir | |
| Dunfermline Athletic | 5-2 | Morton | |
| Duns | 4-1 | Girvan | |
| East Fife | 1-2 | Montrose | |
| Edinburgh City (old) | 3-3 | Stranraer | |
| Falkirk | 5-0 | Brechin City | |
| Falkirk Amateurs | 2-4 | Elgin City | |
| Forfar Athletic | 0-3 | Hibernian | |
| Heart of Midlothian | 14-2 | Penicuik Athletic | |
| Huntly | 1-8 | Motherwell | |
| Kilmarnock | 6-1 | Berwick Rangers | |
| King's Park | 5-5 | Babcock and Wilcox | |
| Leith Athletic | 0-2 | Airdrieonians | |
| Nithsdale Wanderers | 5-5 | Buckie Thistle | |
| Queen of the South | 5-4 | Arbroath | |
| Queen's Park | 4-1 | St Cuthberts Wndrs | |
| Raith Rovers | 0-1 | Rangers | |
| St Mirren | 7-0 | East Stirlingshire | |
| Third Lanark | 8-2 | Inverness Clachn'din | |
» Scottish FA Cup 1938-1939 : Results
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