22nd October 1989
| Final | Aberdeen | 2-1 | Rangers |
20th September 1989
| Semi Final | Aberdeen | 1-0 | Celtic |
19th September 1989
| Semi Final | Rangers | 5-0 |
30th August 1989
| Quarter Final | Heart of Midlothian | 2-2 | Celtic |
| Quarter Final | 0-3 | Rangers |
| Quarter Final | Aberdeen | 3-1 | St. Mirren |
29th August 1989
| Quarter Final | Hibernian | 1-3 |
23rd August 1989
| 3rd Round | St. Mirren | 1-0 | Motherwell |
| 3rd Round | 1-2 | Rangers |
| 3rd Round | 2-1 | Dundee United |
| 3rd Round | 1-4 | Heart of Midlothian |
| 3rd Round | 1-0 |
| 3rd Round | Aberdeen | 4-0 |
22nd August 1989
| 3rd Round | Hibernian | 0-0 |
| 3rd Round | Celtic | 2-0 |
16th August 1989
| 2nd Round | 1-0 |
| 2nd Round | Heart of Midlothian | 3-0 |
| 2nd Round | Dundee United | 1-0 |
| 2nd Round | 3-1 | Livingston |
| 2nd Round | 0-3 |
| 2nd Round | 0-2 | Aberdeen |
15th August 1989
| 2nd Round | Rangers | 4-0 |
| 2nd Round | 0-1 |
| 2nd Round | Kilmarnock | 1-4 | Motherwell |
| 2nd Round | Hibernian | 2-0 |
| 2nd Round | 3-0 |
| 2nd Round | 5-1 |
| 2nd Round | 0-3 | Celtic |
| 2nd Round | 0-2 | St. Mirren |
| 2nd Round | 0-1 |
| 2nd Round | 4-0 |
9th August 1989
| 1st Round | 3-4 |
| 1st Round | 0-3 |
| 1st Round | 2-2 |
| 1st Round | 0-4 |
| 1st Round | 1-0 |
8th August 1989
| 1st Round | 3-0 |