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| 18.09.2009 | 20:30 | Annan Athletic | - | East Stirlingshire FC | 1:0 | |
| 20:30 | Cowdenbeath FC | - | Dundee FC | 0:3 | ||
| 20:30 | Inverness CT | - | Stranraer FC | 3:0 | ||
| 20:30 | Ross County FC | - | Greenock Morton FC | 2:1 | ||
| 20:30 | Stirling Albion FC | - | Stenhousemuir FC | 3:1 | ||
| 20:45 | Dunfermline Athletic | - | Queen Of The South | 1:2 | ||
| 20:45 | Elgin City | - | Albion Rovers | 3:0 | ||
| 20:45 | Forfar Athletic | - | Partick Thistle | 1:6 |
