| Saturday 8th January 2011 | |||
| Aberdeen | 6-0 | East Fife | |
| Dundee United | 0-0 | Ross County | |
| Hamilton Academical | 2-0 | Alloa Athletic | |
| Hibernian | 0-0 | Ayr United | |
| Inverness CT | 2-0 | Elgin City | |
| Montrose | 2-2 | Dunfermline Athletic | |
| St Mirren | 0-0 | Peterhead | |
| Sunday 9th January 2011 | |||
| Berwick Rangers | 0-2 | Celtic | |
| Dundee | 0-4 | Motherwell | |
| Monday 10th January 2011 | |||
| Rangers | 3-0 | Kilmarnock | |
| Tuesday 11th January 2011 | |||
| Falkirk | 2-2 | Partick Thistle | |
| Heart of Midlothian | 0-1 | St Johnstone | |
| Queen of the South | 1-2 | Brechin City | |
| Tuesday 18th January 2011 | |||
| Morton | 2-2 | Airdrie United | |
| Stenhousemuir | 0-0 | Stranraer | |
| Replay | |||
| Ayr United | 1-0 | Hibernian | |
| Dunfermline Athletic | 5-3 | Montrose | |
| Partick Thistle | 1-0 | Falkirk | |
| Peterhead | 1-6 | St Mirren | |
| Ross County | 0-0 | Dundee United | aet |
| (Dundee United won on penalties) | |||
| Wednesday 19th January 2011 | |||
| East Stirlingshire | 1-0 | Buckie Thistle | |
| (Buckie Thistle won - East Stirlingshire disqualified) | |||
| Tuesday 25th January 2011 | |||
| Replay | |||
| Airdrie United | 2-5 | Morton | |
| Stranraer | 4-3 | Stenhousemuir | |









