27th May 2000
| Final | Rangers | 4-0 | Aberdeen |
9th April 2000
| Semi Final | Aberdeen | 2-1 | Hibernian |
8th April 2000
| Semi Final | Rangers | 7-0 | Ayr United |
12th March 2000
| 5th Round | Rangers | 4-1 | Heart of Midlothian |
| 5th Round | Dundee United | 0-1 | Aberdeen |
11th March 2000
| 5th Round | Hibernian | 3-1 | Falkirk |
| 5th Round | Ayr United | 2-0 | Partick Thistle |
29th February 2000
| 4th Round Replay | Falkirk | 3-0 |
| 4th Round Replay | 0-3 | Hibernian |
| 4th Round Replay | Aberdeen | 1-0 | Inverness Caledonian Thistle |
26th February 2000
| 4th Round | Motherwell | 3-4 | Ayr United |
22nd February 2000
| 4th Round Replay | Dundee United | 4-0 | Alloa Athletic |
20th February 2000
| 4th Round | Inverness Caledonian Thistle | 1-1 | Aberdeen |
19th February 2000
| 4th Round | Partick Thistle | 2-1 | Livingston |
| 4th Round | Greenock Morton | 0-1 | Rangers |
| 4th Round | Hibernian | 1-1 |
| 4th Round | Clyde | 0-2 | Heart of Midlothian |
| 4th Round | 0-0 | Falkirk |
| 4th Round | Alloa Athletic | 2-2 | Dundee United |
| 3rd Round Replay | Motherwell | 2-0 | Arbroath |
15th February 2000
| 3rd Round Replay | Ayr United | 1-1 | Dundee |
9th February 2000
| 3rd Round Replay | Alloa Athletic | 1-0 | Kilmarnock |
8th February 2000
| 3rd Round | Celtic | 1-3 | Inverness Caledonian Thistle |
| 3rd Round Replay | Brechin City | 0-0 | Greenock Morton |
| 3rd Round Replay | Aberdeen | 2-0 | St. Mirren |
5th February 2000
| 3rd Round | Kilmarnock | 0-0 | Alloa Athletic |
30th January 2000
| 3rd Round | St. Johnstone | 0-2 | Rangers |
| 3rd Round | Greenock Morton | 1-1 | Brechin City |
| 3rd Round | Dundee United | 4-1 | Airdrie United |
29th January 2000
| 3rd Round | Stranraer | 1-2 |
| 3rd Round | St. Mirren | 1-1 | Aberdeen |
| 3rd Round | Queen of the South | 0-7 | Livingston |
| 3rd Round | Hibernian | 4-1 | Dunfermline Athletic |
| 3rd Round | Heart of Midlothian | 3-2 | Stenhousemuir |
| 3rd Round | Falkirk | 3-1 | Peterhead |
| 3rd Round | Dundee | 0-0 | Ayr United |
| 3rd Round | 1-0 | Stirling Albion |
| 3rd Round | Clyde | 3-1 | Raith Rovers |
| 3rd Round | Arbroath | 9-9 | Motherwell |
| 3rd Round | Albion Rovers | 1-2 | Partick Thistle |
| 2nd Round Replay | Alloa Athletic | 2-0 |
19th January 2000
| 2nd Round Replay | 1-5 | Albion Rovers |
15th January 2000
| 2nd Round Replay | 1-3 | Arbroath |
| 2nd Round Replay | Annan Athletic | 2-3 | Brechin City |
8th January 2000
| 2nd Round | 2-2 | Alloa Athletic |
| 2nd Round | Stranraer | 1-0 |
| 2nd Round | Stirling Albion | 2-1 | East Fife |
| 2nd Round | Queen's Park | 1-2 |
| 2nd Round | Peterhead | 2-1 | Forfar Athletic |
| 2nd Round | Partick Thistle | 2-1 |
| 2nd Round | Montrose | 1-3 | Queen of the South |
| 2nd Round | Dumbarton | 0-2 | Stenhousemuir |
| 2nd Round | Cowdenbeath | 2-3 | Clyde |
| 2nd Round | Brechin City | 2-2 | Annan Athletic |
| 2nd Round | Arbroath | 0-0 |
| 2nd Round | Albion Rovers | 0-0 |
3rd January 2000
| 1st Round Replay | Forfar Athletic | 0-0 | Ross County |
27th December 1999
| 1st Round | 1-7 | Stenhousemuir |
11th December 1999
| 1st Round | Ross County | 2-2 | Forfar Athletic |
| 1st Round | 0-1 |
| 1st Round | 1-2 | Clyde |