| Saturday 20th November 2010 | |||
| Airdrie United | 2-2 | Beith | |
| Alloa Athletic | 4-2 | Raith Rovers | |
| Ayr United | 5-0 | Sunnybank | |
| Bo'ness United | 0-2 | Buckie Thistle | |
| Brechin City | 2-2 | Annan Athletic | |
| Cove Rangers | 0-3 | Berwick Rangers | |
| Dumbarton | 1-2 | Morton | |
| East Fife | 3-1 | Forfar Athletic | |
| Elgin City | 2-1 | Livingston | |
| Montrose | 3-1 | Whitehill Welfare | |
| Peterhead | 2-0 | Cowdenbeath | |
| Ross County | 4-1 | Deveronvale | |
| Spartans | 1-2 | East Stirlingshire | |
| Stenhousemuir | 2-2 | Threave Rovers | |
| Stirling Albion | 1-3 | Partick Thistle | |
| Stranraer | 4-2 | Girvan | |
| Tuesday 4th January 2011 | |||
| Replay | |||
| Annan Athletic | 2-5 | Brechin City | |
| Beith | 3-4 | Airdrie United | |
| Wednesday 12th January 2011 | |||
| Replay | |||
| Threave Rovers | 1-5 | Stenhousemuir | |









