26th May 2001
| Final | Celtic | 3-0 | Hibernian |
15th April 2001
| Semi Final | Celtic | 3-1 | Dundee United |
14th April 2001
| Semi Final | Hibernian | 3-0 |
11th March 2001
| 5th Round | Dundee United | 1-0 | Rangers |
| 5th Round | Celtic | 1-0 | Heart of Midlothian |
10th March 2001
| 5th Round | 3-1 | Peterhead |
| 5th Round | Kilmarnock | 0-1 | Hibernian |
7th March 2001
| 4th Round Replay | Dundee | 0-1 | Heart of Midlothian |
| 4th Round Replay | Celtic | 4-1 | Dunfermline Athletic |
6th March 2001
| 4th Round Replay | Kilmarnock | 2-1 | Inverness Caledonian Thistle |
| 4th Round Replay | Aberdeen | 0-1 |
18th February 2001
| 4th Round | Ross County | 2-3 | Rangers |
17th February 2001
| 4th Round | Stirling Albion | 2-3 | Hibernian |
| 4th Round | Peterhead | 0-0 | Airdrie United |
| 4th Round | Motherwell | 0-2 | Dundee United |
| 4th Round | 0-0 | Aberdeen |
| 4th Round | Inverness Caledonian Thistle | 1-1 | Kilmarnock |
| 4th Round | Heart of Midlothian | 1-1 | Dundee |
| 4th Round | Dunfermline Athletic | 2-2 | Celtic |
13th February 2001
| 3rd Round Replay | Dunfermline Athletic | 3-2 | St. Johnstone |
12th February 2001
| 3rd Round | Queen of the South | 1-3 | Airdrie United |
| 3rd Round Replay | Falkirk | 0-2 | Dundee |
7th February 2001
| 3rd Round Replay | Heart of Midlothian | 2-1 |
28th January 2001
| 3rd Round | Stranraer | 1-4 | Celtic |
27th January 2001
| 3rd Round | Stirling Albion | 2-0 | Raith Rovers |
| 3rd Round | St. Mirren | 1-2 | Motherwell |
| 3rd Round | St. Johnstone | 0-0 | Dunfermline Athletic |
| 3rd Round | Ross County | 2-1 |
| 3rd Round | Rangers | 2-0 | Brechin City |
| 3rd Round | Peterhead | 4-1 | Greenock Morton |
| 3rd Round | Montrose | 0-2 | Dundee United |
| 3rd Round | Kilmarnock | 1-0 | Partick Thistle |
| 3rd Round | Inverness Caledonian Thistle | 4-3 | Ayr United |
| 3rd Round | Hibernian | 6-1 | Clyde |
| 3rd Round | East Fife | 1-4 |
| 3rd Round | Dundee | 0-0 | Falkirk |
| 3rd Round | 0-0 | Heart of Midlothian |
| 3rd Round | Alloa Athletic | 0-3 | Aberdeen |
| 2nd Round | Elgin City | 0-1 | Queen of the South |
24th January 2001
| 2nd Round Replay | 0-1 | Montrose |
| 2nd Round Replay | Cowdenbeath | 0-1 |
13th January 2001
| 2nd Round | Montrose | 1-1 |
9th January 2001
| 1st Round Replay | Arbroath | 1-2 | Montrose |
6th January 2001
| 2nd Round | Stranraer | 2-0 | Dumbarton |
| 2nd Round | 1-3 | Stirling Albion |
| 2nd Round | Peterhead | 3-0 | Cove Rangers |
| 2nd Round | Partick Thistle | 3-0 |
| 2nd Round | East Fife | 1-0 | Queen's Park |
| 2nd Round | 2-6 | Brechin City |
| 2nd Round | 2-0 |
| 2nd Round | 3-3 | Cowdenbeath |
| 1st Round | Montrose | 0-0 | Arbroath |
20th December 2000
| 1st Round | Edinburgh City | 0-1 |
18th December 2000
| 1st Round | Queen of the South | 2-0 |
| 1st Round Replay | Peterhead | 3-0 |
16th December 2000
| 1st Round | 0-0 | Peterhead |
12th December 2000
| 1st Round Replay | 0-1 | Dumbarton |
| 1st Round Replay | East Fife | 2-0 | Albion Rovers |
| 1st Round | Brechin City | 3-0 | Forfar Athletic |
9th December 2000
| 1st Round | Stenhousemuir | 1-4 |
| 1st Round | Dumbarton | 1-1 |
| 1st Round | Albion Rovers | 1-1 | East Fife |