19th March 2000
| Final | Celtic | 2-0 | Aberdeen |
16th February 2000
| Semi Final | Celtic | 1-0 | Kilmarnock |
13th February 2000
| Semi Final | Aberdeen | 1-0 | Dundee United |
2nd February 2000
| Quarter Final | Kilmarnock | 1-0 | Heart of Midlothian |
1st December 1999
| Quarter Final | Dundee United | 3-2 | Motherwell |
| Quarter Final | Celtic | 1-0 | Dundee |
| Quarter Final | Aberdeen | 1-0 | Rangers |
13th October 1999
| 3rd Round | Ayr United | 0-4 | Celtic |
12th October 1999
| 3rd Round | St. Johnstone | 1-2 | Dundee United |
| 3rd Round | Rangers | 1-0 | Dunfermline Athletic |
| 3rd Round | Kilmarnock | 3-2 | Hibernian |
| 3rd Round | Inverness Caledonian Thistle | 0-1 | Motherwell |
| 3rd Round | East Fife | 0-2 | Heart of Midlothian |
| 3rd Round | Alloa Athletic | 1-3 | Dundee |
| 3rd Round | Aberdeen | 1-1 | Falkirk |
18th August 1999
| 2nd Round | Raith Rovers | 2-2 | Motherwell |
| 2nd Round | Queen of the South | 1-3 | Heart of Midlothian |
| 2nd Round | 0-2 | Falkirk |
| 2nd Round | Dunfermline Athletic | 4-0 | Queen's Park |
| 2nd Round | Dundee United | 3-1 | Ross County |
17th August 1999
| 2nd Round | Greenock Morton | 1-3 | Alloa Athletic |
| 2nd Round | Inverness Caledonian Thistle | 2-0 | St. Mirren |
| 2nd Round | East Fife | 2-2 | Airdrie United |
| 2nd Round | Dundee | 4-0 | Dumbarton |
| 2nd Round | Clyde | 2-2 | Hibernian |
| 2nd Round | Ayr United | 2-1 |
| 2nd Round | Aberdeen | 1-0 | Livingston |
31st July 1999
| 1st Round | Stranraer | 0-1 | Raith Rovers |
| 1st Round | Stenhousemuir | 1-3 | Inverness Caledonian Thistle |
| 1st Round | Ross County | 2-1 | Forfar Athletic |
| 1st Round | Queen's Park | 2-1 |
| 1st Round | Queen of the South | 1-0 | Arbroath |
| 1st Round | Partick Thistle | 0-2 | Alloa Athletic |
| 1st Round | Montrose | 1-2 |
| 1st Round | East Fife | 2-2 | Stirling Albion |
| 1st Round | Cowdenbeath | 0-2 | Livingston |
| 1st Round | 1-2 |
| 1st Round | Brechin City | 0-2 | Dumbarton |
| 1st Round | Albion Rovers | 0-3 | Clyde |