18th February 2014
| 5th Round Replay | Inverness Caledonian Thistle | 2-0 | Stranraer |
9th February 2014
| 5th Round | Dundee United | 2-1 | St. Mirren |
8th February 2014
| 5th Round | Stranraer | 2-2 | Inverness Caledonian Thistle |
| 5th Round | Hibernian | 2-3 | Raith Rovers |
| 5th Round | Forfar Athletic | 0-4 | St. Johnstone |
| 5th Round | Alloa Athletic | 0-1 | Dumbarton |
| 5th Round | Albion Rovers | 2-0 | Stenhousemuir |
| 5th Round | Celtic | 1-2 | Aberdeen |
10th December 2013
| 4th Round Replay | Forfar Athletic | 3-3 | Brechin City |
| 4th Round Replay | St. Mirren | 3-0 | Queen of the South |
| 4th Round Replay | Stranraer | 4-1 | Clyde |
4th December 2013
| 4th Round Replay | Dunfermline Athletic | 1-0 | Ayr United |
1st December 2013
| 4th Round | Partick Thistle | 0-1 | Aberdeen |
| 4th Round | Heart of Midlothian | 0-7 | Celtic |
30th November 2013
| 4th Round | Ayr United | 1-1 | Dunfermline Athletic |
| 4th Round | Clyde | 1-1 | Stranraer |
| 4th Round | Ross County | 0-1 | Hibernian |
| 4th Round | Queen of the South | 2-2 | St. Mirren |
| 4th Round | Stenhousemuir | 3-0 |
| 4th Round | Dundee | 0-1 | Raith Rovers |
| 4th Round | St. Johnstone | 2-0 |
| 4th Round | Inverness Caledonian Thistle | 4-0 | Greenock Morton |
| 4th Round | Falkirk | 0-2 | Rangers |
| 4th Round | Brechin City | 1-3 | Forfar Athletic |
| 4th Round | Albion Rovers | 1-0 | Motherwell |
| 4th Round | Alloa Athletic | 3-2 | Stirling Albion |
29th November 2013
| 4th Round | Dundee United | 5-2 | Kilmarnock |
12th November 2013
| 3rd Round Replay | Annan Athletic | 2-4 | Stenhousemuir |
9th November 2013
| 3rd Round | 2-3 | Stranraer |
| 3rd Round | 3-1 |
3rd November 2013
| 3rd Round | 0-2 | Raith Rovers |
2nd November 2013
| 3rd Round | Queen of the South | 1-0 |
| 3rd Round | Clyde | 2-1 |
| 3rd Round | Albion Rovers | 1-0 |
| 3rd Round | Arbroath | 0-2 | Brechin City |
| 3rd Round | Stenhousemuir | 2-2 | Annan Athletic |
| 3rd Round | 2-1 | Montrose |
| 3rd Round | 0-3 | Stirling Albion |
1st November 2013
| 3rd Round | Rangers | 3-0 |
19th October 2013
| 2nd Round Replay | Annan Athletic | 4-0 |
12th October 2013
| 2nd Round Replay | 2-0 | Edinburgh City |
| 2nd Round Replay | Cove Rangers | 0-3 |
| 2nd Round Replay | 1-2 | Stirling Albion |
| 2nd Round Replay | 1-2 | Queen's Park |
| 2nd Round Replay | 1-3 |
6th October 2013
| 2nd Round | 6-0 |
5th October 2013
| 2nd Round | 1-1 | Cove Rangers |
| 2nd Round | 0-1 | Montrose |
| 2nd Round | Edinburgh City | 4-4 |
| 2nd Round | 2-1 | Peterhead |
| 2nd Round | 0-4 | Elgin City |
| 2nd Round | Stirling Albion | 2-2 |
| 2nd Round | 4-0 |
| 2nd Round | 0-2 |
| 2nd Round | 0-0 | Annan Athletic |
| 2nd Round | Queen's Park | 2-2 |
| 2nd Round | 0-6 |
| 2nd Round | 2-2 |
| 2nd Round | 0-3 | Clyde |
| 2nd Round | 4-2 |
| 2nd Round | Albion Rovers | 1-0 |
21st September 2013
| 1st Round Replay | 3-1 |
| 1st Round Replay | 3-1 |
14th September 2013
| 1st Round | 2-0 |
| 1st Round | 0-2 |
| 1st Round | 3-0 |
| 1st Round | 0-4 | Edinburgh City |
| 1st Round | 3-4 |
| 1st Round | 0-6 |
| 1st Round | 1-5 |
| 1st Round | 3-0 |
| 1st Round | 1-3 |
| 1st Round | 0-0 |
| 1st Round | 4-5 |
| 1st Round | 4-0 |
| 1st Round | 3-1 |
| 1st Round | 3-4 |
| 1st Round | 1-0 |
| 1st Round | 5-0 |
| 1st Round | 0-1 |
| 1st Round | 0-0 |