15th March 2009
| Final | Rangers | 0-2 | Celtic |
28th January 2009
| Semi Final | Celtic | 0-0 | Dundee United |
27th January 2009
| Semi Final | Rangers | 3-0 | Falkirk |
29th October 2008
| Quarter Final | Kilmarnock | 1-3 | Celtic |
28th October 2008
| Quarter Final | Rangers | 2-0 |
| Quarter Final | Falkirk | 1-0 | Inverness Caledonian Thistle |
| Quarter Final | Dundee United | 1-0 | Dunfermline Athletic |
24th September 2008
| 3rd Round | Kilmarnock | 4-2 | Aberdeen |
| 3rd Round | Motherwell | 1-2 |
| 3rd Round | Partick Thistle | 1-2 | Rangers |
23rd September 2008
| 3rd Round | Dundee United | 2-0 | Airdrie United |
| 3rd Round | Dunfermline Athletic | 2-0 | St. Mirren |
| 3rd Round | Falkirk | 2-1 | Queen of the South |
| 3rd Round | Celtic | 4-0 | Livingston |
| 3rd Round | Greenock Morton | 1-2 | Inverness Caledonian Thistle |
27th August 2008
| 2nd Round | Brechin City | 0-2 | Kilmarnock |
| 2nd Round | Heart of Midlothian | 0-0 | Airdrie United |
| 2nd Round | Ayr United | 0-1 | Aberdeen |
| 2nd Round | Arbroath | 2-2 | Inverness Caledonian Thistle |
26th August 2008
| 2nd Round | Dunfermline Athletic | 1-0 | Alloa Athletic |
| 2nd Round | Hibernian | 3-4 | Greenock Morton |
| 2nd Round | Raith Rovers | 1-3 | Falkirk |
| 2nd Round | Cowdenbeath | 1-5 | Dundee United |
| 2nd Round | St. Mirren | 7-0 | Dumbarton |
| 2nd Round | Dundee | 1-2 | Partick Thistle |
| 2nd Round | Livingston | 2-1 | St. Johnstone |
| 2nd Round | 3-1 | Clyde |
6th August 2008
| 1st Round | Ayr United | 2-1 |
| 1st Round | East Fife | 0-3 | Brechin City |
| 1st Round | 1-2 | Livingston |
| 1st Round | Arbroath | 3-2 | Stirling Albion |
5th August 2008
| 1st Round | Ross County | 2-3 | Airdrie United |
| 1st Round | Alloa Athletic | 2-0 | Elgin City |
| 1st Round | Partick Thistle | 4-3 | Forfar Athletic |
| 1st Round | Peterhead | 0-2 | Dunfermline Athletic |
| 1st Round | Stranraer | 3-6 | Greenock Morton |
| 1st Round | Montrose | 0-2 | Cowdenbeath |
| 1st Round | Clyde | 4-1 | Queen's Park |
| 1st Round | Albion Rovers | 0-0 | Raith Rovers |
| 1st Round | Stenhousemuir | 1-5 | St. Johnstone |
| 1st Round | Dumbarton | 1-1 | Annan Athletic |