| Saturday 28th November 2009 | |||
| Airdrie United | 4-0 | Queen of the South | |
| Albion Rovers | 1-0 | Elgin City | |
| Cowdenbeath | 0-0 | Alloa Athletic | |
| Deveronvale | 0-1 | Ayr United | |
| Edinburgh City | 3-1 | Keith | |
| Irvine Meadow | 1-0 | Arbroath | |
| Montrose | 2-1 | East Fife | |
| Morton | 0-0 | Dumbarton | |
| Raith Rovers | 0-0 | Peterhead | |
| Ross County | 5-1 | Berwick Rangers | |
| Spartans | 0-1 | Forfar Athletic | |
| Stirling Albion | 2-1 | Auchinleck Talbot | |
| Threave Rovers | 1-2 | Inverurie Locos | |
| Wick Academy | 4-4 | Brechin City | |
| Tuesday 1st December 2009 | |||
| Replay | |||
| Peterhead | 1-4 | Raith Rovers | |
| Saturday 5th December 2009 | |||
| Stenhousemuir | 5-0 | Cove Rangers | |
| Replay | |||
| Dumbarton | 0-1 | Morton | |
| Tuesday 8th December 2009 | |||
| Replay | |||
| Alloa Athletic | 1-0 | Cowdenbeath | |
| Brechin City | 4-2 | Wick Academy | |
| Wednesday 9th December 2009 | |||
| Clyde | 1-1 | Livingston | |
| Monday 14th December 2009 | |||
| Replay | |||
| Livingston | 7-1 | Clyde | |
