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| 28/11/2009 | 13:30 | Irvine Meadow XI | - | Arbroath FC | 1:0 | |
| 15:00 | Airdrie United FC | - | Queen Of The South | 4:0 | ||
| 15:00 | Albion Rovers | - | Elgin City | 1:0 | ||
| 15:00 | Cowdenbeath FC | - | Alloa Athletic | 0:0 | ||
| 15:00 | Deveronvale FC | - | Ayr United | 0:1 | ||
| 15:00 | Edinburgh City FC | - | Keith FC | 3:1 | ||
| 15:00 | Montrose FC | - | East Fife FC | 2:1 | ||
| 15:00 | Greenock Morton FC | - | Dumbarton FC | 0:0 | ||
| 15:00 | Raith Rovers | - | Peterhead FC | 0:0 | ||
| 15:00 | Ross County FC | - | Berwick Rangers | 5:1 | ||
| 15:00 | The Spartans FC | - | Forfar Athletic | 0:1 | ||
| 15:00 | Stirling Albion FC | - | Auchinleck Talbot | 2:1 | ||
| 15:00 | Threave Rovers | - | Inverurie Loco Works | 1:2 | ||
| 15:00 | Wick Academy FC | - | Brechin City FC | 4:4 | ||
| 05/12/2009 | 15:00 | Stenhousemuir FC | - | Cove Rangers | 5:0 | |
| 09/12/2009 | 19:45 | Clyde FC | - | Livingston FC | 1:1 | |
| decisive matches | ||||||
|---|---|---|---|---|---|---|
| 01/12/2009 | 19:45 | Peterhead FC | - | Raith Rovers | 1:4 | |
| 05/12/2009 | 15:00 | Dumbarton FC | - | Greenock Morton FC | 0:1 | |
| 08/12/2009 | 19:45 | Alloa Athletic | - | Cowdenbeath FC | 1:0 | |
| 19:45 | Brechin City FC | - | Wick Academy FC | 4:2 | ||
| 14/12/2009 | 19:45 | Livingston FC | - | Clyde FC | 7:1 | |
