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 | 0-4 | Celtic |
12th October 1999
| 3rd Round | 1-2 | Dundee United |
| 3rd Round | Rangers | 1-0 |
| 3rd Round | Kilmarnock | 3-2 | Hibernian |
| 3rd Round | 0-1 | Motherwell |
| 3rd Round | 0-2 | Heart of Midlothian |
| 3rd Round | 1-3 | Dundee |
| 3rd Round | Aberdeen | 1-1 | Falkirk |
18th August 1999
| 2nd Round | 2-2 | Motherwell |
| 2nd Round | 1-3 | Heart of Midlothian |
| 2nd Round | 0-2 | Falkirk |
| 2nd Round | 4-0 |
| 2nd Round | Dundee United | 3-1 |
17th August 1999
| 2nd Round | 1-3 |
| 2nd Round | 2-0 | St. Mirren |
| 2nd Round | 2-2 |
| 2nd Round | Dundee | 4-0 |
| 2nd Round | 2-2 | Hibernian |
| 2nd Round | 2-1 |
| 2nd Round | Aberdeen | 1-0 | Livingston |
31st July 1999
| 1st Round | 0-1 |
| 1st Round | 1-3 |
| 1st Round | 2-1 |
| 1st Round | 2-1 |
| 1st Round | 1-0 |
| 1st Round | 0-2 |
| 1st Round | 1-2 |
| 1st Round | 2-2 |
| 1st Round | 0-2 | Livingston |
| 1st Round | 1-2 |
| 1st Round | 0-2 |
| 1st Round | 0-3 |