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| 24/10/2009 | 15:00 | Queen's Park FC | - | Livingston FC | 1:3 | |
| 15:00 | Nairn County FC | - | Elgin City | 2:4 | ||
| 15:00 | Fraserburgh FC | - | The Spartans FC | 1:4 | ||
| 15:00 | Deveronvale FC | - | Buckie Thistle | 2:2 | ||
| 15:00 | Whitehill Welfare | - | Threave Rovers | 1:1 | ||
| 15:00 | Inverurie Loco Works | - | Stranraer FC | 2:1 | ||
| 15:00 | Vale of Leithen FC | - | Keith FC | 1:3 | ||
| 15:00 | Forfar Athletic | - | East Stirlingshire FC | 4:2 | ||
| 15:00 | Cove Rangers | - | Annan Athletic | 2:1 | ||
| 15:00 | Selkirk FC | - | Irvine Meadow XI | 0:3 | ||
| 15:00 | Girvan FC | - | Wick Academy FC | 1:4 | ||
| 15:00 | Lossiemouth FC | - | Albion Rovers | 0:2 | ||
| 15:00 | Edinburgh City FC | - | Burntisland Shipyard | 5:1 | ||
| 15:00 | Banks O’ Dee FC | - | Montrose FC | 0:3 | ||
| 15:00 | Huntly FC | - | Auchinleck Talbot | 1:1 | ||
| 15:00 | Civil Service Strollers | - | Berwick Rangers | 1:2 | ||
| decisive matches | ||||||
|---|---|---|---|---|---|---|
| 31/10/2009 | 15:00 | Threave Rovers | - | Whitehill Welfare | 1:0 | |
| 15:00 | Auchinleck Talbot | - | Huntly FC | 4:3 | ||
| 15:00 | Buckie Thistle | - | Deveronvale FC | 1:2 aet | ||
