20th May 1989
| Final | Celtic | 1-0 | Rangers |
18th April 1989
| Semi Final Replay | Rangers | 4-0 |
16th April 1989
| Semi Final | Celtic | 3-1 | Hibernian |
15th April 1989
| Semi Final | Rangers | 0-0 |
27th March 1989
| 5th Round Replay | 3-2 |
| 5th Round Replay | Dundee United | 0-1 | Rangers |
22nd March 1989
| 5th Round | 2-2 |
21st March 1989
| 5th Round | Rangers | 2-2 | Dundee United |
18th March 1989
| 5th Round | Hibernian | 1-0 |
| 5th Round | Celtic | 2-1 | Heart of Midlothian |
27th February 1989
| 4th Round 2nd Replay | Dundee United | 1-0 | Aberdeen |
22nd February 1989
| 4th Round Replay | Dundee United | 1-1 | Aberdeen |
| 4th Round Replay | 4-2 |
18th February 1989
| 4th Round | 2-1 |
| 4th Round | Rangers | 8-0 |
| 4th Round | 0-0 |
| 4th Round | Livingston | 0-1 |
| 4th Round | Hibernian | 2-1 | Motherwell |
| 4th Round | Heart of Midlothian | 2-0 |
| 4th Round | Celtic | 4-1 |
| 4th Round | Aberdeen | 1-1 | Dundee United |
1st February 1989
| 3rd Round Replay | 1-0 |
| 3rd Round Replay | Rangers | 3-0 |
| 3rd Round Replay | Motherwell | 2-1 |
| 3rd Round Replay | Kilmarnock | 0-1 |
| 3rd Round Replay | 0-1 |
| 3rd Round Replay | Aberdeen | 3-1 |
31st January 1989
| 3rd Round Replay | St. Mirren | 1-3 |
| 3rd Round Replay | 0-1 |
29th January 1989
| 3rd Round | Livingston | 2-0 |
28th January 1989
| 3rd Round | 2-0 |
| 3rd Round | 1-1 | Rangers |
| 3rd Round | 0-0 |
| 3rd Round | 2-2 | Kilmarnock |
| 3rd Round | 0-0 | St. Mirren |
| 3rd Round | 0-0 |
| 3rd Round | Hibernian | 1-0 |
| 3rd Round | Heart of Midlothian | 4-1 |
| 3rd Round | 1-1 |
| 3rd Round | 1-1 | Motherwell |
| 3rd Round | 0-0 | Aberdeen |
| 3rd Round | 1-2 | Dundee United |
| 3rd Round | 2-1 |
| 3rd Round | Celtic | 2-0 |
| 3rd Round | 3-1 |
14th January 1989
| 2nd Round Replay | 3-2 |
| 2nd Round Replay | 4-0 |
| 2nd Round Replay | 2-1 |
| 2nd Round Replay | 2-0 |
| 2nd Round Replay | 1-0 |
7th January 1989
| 2nd Round | 2-1 |
| 2nd Round | 1-1 |
| 2nd Round | 1-1 |
| 2nd Round | 2-2 |
| 2nd Round | 1-2 |
| 2nd Round | 1-1 |
| 2nd Round | 1-1 |
| 2nd Round | 1-5 |
10th December 1988
| 1st Round Replay | 0-1 |
| 1st Round Replay | 2-1 |
7th December 1988
| 1st Round Replay | 2-1 |
3rd December 1988
| 1st Round | 2-2 |
| 1st Round | 2-0 |
| 1st Round | 0-0 |
| 1st Round | 1-0 |
| 1st Round | 4-1 |
| 1st Round | 1-1 |