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 |
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 |
| 5th Round | 2-0 |
29th February 2000
| 4th Round Replay | 3-0 |
| 4th Round Replay | 0-3 | Hibernian |
| 4th Round Replay | Aberdeen | 1-0 |
26th February 2000
| 4th Round | Motherwell | 3-4 |
22nd February 2000
| 4th Round Replay | Dundee United | 4-0 |
20th February 2000
| 4th Round | 1-1 | Aberdeen |
19th February 2000
| 4th Round | 2-1 | Livingston |
| 4th Round | 0-1 | Rangers |
| 4th Round | Hibernian | 1-1 |
| 4th Round | 0-2 | Heart of Midlothian |
| 4th Round | 0-0 |
| 4th Round | 2-2 | Dundee United |
| 3rd Round Replay | Motherwell | 2-0 |
15th February 2000
| 3rd Round Replay | 1-1 |
9th February 2000
| 3rd Round Replay | 1-0 | Kilmarnock |
8th February 2000
| 3rd Round | Celtic | 1-3 |
| 3rd Round Replay | 0-0 |
| 3rd Round Replay | Aberdeen | 2-0 | St. Mirren |
5th February 2000
| 3rd Round | Kilmarnock | 0-0 |
30th January 2000
| 3rd Round | 0-2 | Rangers |
| 3rd Round | 1-1 |
| 3rd Round | Dundee United | 4-1 |
29th January 2000
| 3rd Round | 1-2 |
| 3rd Round | St. Mirren | 1-1 | Aberdeen |
| 3rd Round | 0-7 | Livingston |
| 3rd Round | Hibernian | 4-1 |
| 3rd Round | Heart of Midlothian | 3-2 |
| 3rd Round | 3-1 |
| 3rd Round | 0-0 |
| 3rd Round | 1-0 |
| 3rd Round | 3-1 |
| 3rd Round | 9-9 | Motherwell |
| 3rd Round | 1-2 |
| 2nd Round Replay | 2-0 |
19th January 2000
| 2nd Round Replay | 1-5 |
15th January 2000
| 2nd Round Replay | 1-3 |
| 2nd Round Replay | 2-3 |
8th January 2000
| 2nd Round | 2-2 |
| 2nd Round | 1-0 |
| 2nd Round | 2-1 |
| 2nd Round | 1-2 |
| 2nd Round | 2-1 |
| 2nd Round | 2-1 |
| 2nd Round | 1-3 |
| 2nd Round | 0-2 |
| 2nd Round | 2-3 |
| 2nd Round | 2-2 |
| 2nd Round | 0-0 |
| 2nd Round | 0-0 |
3rd January 2000
| 1st Round Replay | 0-0 |
27th December 1999
| 1st Round | 1-7 |
11th December 1999
| 1st Round | 2-2 |
| 1st Round | 0-1 |
| 1st Round | 1-2 |