18th March 2001
| Final | Celtic | 3-0 | Kilmarnock |
7th February 2001
| Semi Final | Celtic | 3-1 | Rangers |
6th February 2001
| Semi Final | Kilmarnock | 3-0 | St. Mirren |
1st November 2000
| Quarter Final | Heart of Midlothian | 2-5 | Celtic |
31st October 2000
| Quarter Final | St. Mirren | 2-1 | Dunfermline Athletic |
| Quarter Final | Rangers | 2-0 | Dundee United |
| Quarter Final | Kilmarnock | 2-1 | Hibernian |
6th September 2000
| 3rd Round | Rangers | 4-2 | Aberdeen |
| 3rd Round | 0-2 | Heart of Midlothian |
| 3rd Round | Falkirk | 1-2 | Hibernian |
| 3rd Round | Dunfermline Athletic | 2-0 | Motherwell |
5th September 2000
| 3rd Round | St. Mirren | 3-0 | Dundee |
| 3rd Round | St. Johnstone | 0-1 | Kilmarnock |
| 3rd Round | Dundee United | 0-0 | Airdrie United |
| 3rd Round | Celtic | 4-0 | Raith Rovers |
23rd August 2000
| 2nd Round | Dundee | 3-0 | Montrose |
22nd August 2000
| 2nd Round | Stenhousemuir | 1-2 | Hibernian |
| 2nd Round | St. Johnstone | 3-1 | Cowdenbeath |
| 2nd Round | Ross County | 1-3 | St. Mirren |
| 2nd Round | Raith Rovers | 2-1 | Arbroath |
| 2nd Round | Queen's Park | 0-3 | Motherwell |
| 2nd Round | Inverness Caledonian Thistle | 0-2 | Airdrie United |
| 2nd Round | Falkirk | 3-1 | Queen of the South |
| 2nd Round | Dunfermline Athletic | 1-0 |
| 2nd Round | Dumbarton | 0-4 |
| 2nd Round | Clyde | 1-2 | Kilmarnock |
| 2nd Round | Alloa Athletic | 0-3 | Dundee United |
9th August 2000
| 1st Round | Dumbarton | 0-0 | Ayr United |
8th August 2000
| 1st Round | Stirling Albion | 0-1 | Stenhousemuir |
| 1st Round | Ross County | 1-0 | Albion Rovers |
| 1st Round | Queen's Park | 2-0 | Stranraer |
| 1st Round | Queen of the South | 2-1 | Forfar Athletic |
| 1st Round | Peterhead | 2-3 | Inverness Caledonian Thistle |
| 1st Round | Partick Thistle | 1-2 | Airdrie United |
| 1st Round | Montrose | 1-0 |
| 1st Round | 2-1 |
| 1st Round | East Fife | 1-2 | Raith Rovers |
| 1st Round | Cowdenbeath | 3-0 | Elgin City |
| 1st Round | 0-2 | Alloa Athletic |
| 1st Round | Clyde | 5-1 | Greenock Morton |
| 1st Round | Arbroath | 2-0 | Brechin City |