| Saturday 23rd January 1909 | |||
| First Round | |||
| Alloa Athletic | 2-2 | St Mirren | |
| Broxburn Athletic | 1-1 | Beith | |
| Clyde | 4-0 | Dykehead (Shotts) | |
| Dundee | 9-0 | Ayr Parkhouse | |
| Falkirk | 2-1 | East Stirlingshire | |
| Hamilton Academical | 0-0 | Queen's Park | |
| Heart of Midlothian | 2-1 | Kilmarnock | |
| Hibernian | 2-1 | Ayr FC | |
| Leith Athletic | 2-4 | Celtic | |
| Morton | 0-4 | Aberdeen | |
| Motherwell | 6-1 | Elgin City | |
| Port Glasgow Ath | 5-0 | Dunblane | |
| St Johnstone | 0-3 | Rangers | |
| Third Lanark | 5-1 | Brechin City | |
| Vale of Leven | 0-0 | Airdrieonians | |
| West Calder Swifts | 0-0 | Partick Thistle | |
» Scottish FA Cup 1908-1909 : Results
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