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| 09/01/2010 | 15:00 | St. Mirren FC | - | Alloa Athletic | 3:1 | |
| 15:00 | Hibernian FC | - | Irvine Meadow XI | 3:0 | ||
| 15:00 | Aberdeen FC | - | Heart of Midlothian | 2:0 | ||
| 15:00 | Partick Thistle | - | Dundee United | 0:2 | ||
| 10/01/2010 | 12:15 | Hamilton Academical | - | Rangers FC | 3:3 | |
| 18/01/2010 | 19:45 | Kilmarnock FC | - | Falkirk FC | 1:0 | |
| 19:45 | Forfar Athletic | - | St. Johnstone FC | 0:3 | ||
| 19:45 | Albion Rovers | - | Stirling Albion FC | 0:0 | ||
| 19:45 | Ross County FC | - | Inverurie Loco Works | 4:0 | ||
| 19:45 | Inverness CT | - | Motherwell FC | 2:0 | ||
| 19:45 | Ayr United | - | Brechin City FC | 1:0 | ||
| 19:45 | Edinburgh City FC | - | Montrose FC | 1:3 | ||
| 19/01/2010 | 19:45 | Greenock Morton FC | - | Celtic FC | 0:1 | |
| 20/01/2010 | 19:45 | Livingston FC | - | Dundee FC | 0:1 | |
| 25/01/2010 | 19:45 | Raith Rovers | - | Airdrie United FC | 1:1 | |
| decisive matches | ||||||
|---|---|---|---|---|---|---|
| 19/01/2010 | 19:45 | Rangers FC | - | Hamilton Academical | 2:0 aet | |
| 20/01/2010 | 19:30 | Stirling Albion FC | - | Albion Rovers | 3:1 | |
| 26/01/2010 | 19:30 | Stenhousemuir FC | - | Dunfermline Athletic | 1:2 aet | |
| 27/01/2010 | 19:45 | Airdrie United FC | - | Raith Rovers | 1:3 | |
