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| 25/07/2009 | 15:00 | Dunfermline Athletic | - | Arbroath FC | 2:1 | |
| 15:00 | East Fife FC | - | Forfar Athletic | 0:2 | ||
| 15:00 | Elgin City | - | Brechin City FC | 3:1 | ||
| 15:00 | Inverness CT | - | Montrose FC | 5:3 pso | ||
| 15:00 | Peterhead FC | - | Cowdenbeath FC | 1:2 | ||
| 15:00 | Ross County FC | - | Alloa Athletic | 3:2 aet | ||
| 15:00 | Stirling Albion FC | - | Raith Rovers | 2:1 | ||
| 15:00 | Airdrie United FC | - | Partick Thistle | 0:1 | ||
| 15:00 | Annan Athletic | - | Queen's Park FC | 2:0 | ||
| 15:00 | Ayr United | - | Albion Rovers | 0:2 | ||
| 15:00 | Queen Of The South | - | Livingston FC | 1:0 | ||
| 15:00 | Stenhousemuir FC | - | Clyde FC | 2:0 | ||
| 15:00 | Stranraer FC | - | Berwick Rangers | 4:2 | ||
| 26/07/2009 | 15:00 | Dumbarton FC | - | Greenock Morton FC | 0:1 |
