23rd October 1988
| Final | Rangers | 3-2 | Aberdeen |
21st September 1988
| Semi Final | Rangers | 3-0 | Heart of Midlothian |
20th September 1988
| Semi Final | Aberdeen | 2-0 | Dundee United |
31st August 1988
| Quarter Final | Dundee United | 2-0 | Celtic |
| Quarter Final | Rangers | 4-1 |
| Quarter Final | 1-4 | Heart of Midlothian |
| Quarter Final | Hibernian | 1-2 | Aberdeen |
24th August 1988
| 3rd Round | 2-1 |
| 3rd Round | Celtic | 7-2 |
| 3rd Round | Rangers | 6-0 |
| 3rd Round | 2-1 | Motherwell |
| 3rd Round | St. Mirren | 1-3 | Dundee United |
23rd August 1988
| 3rd Round | 1-2 | Aberdeen |
| 3rd Round | Hibernian | 1-0 | Kilmarnock |
| 3rd Round | Livingston | 0-2 | Heart of Midlothian |
17th August 1988
| 2nd Round | 2-0 |
| 2nd Round | 5-1 |
| 2nd Round | 1-1 |
| 2nd Round | 1-1 |
| 2nd Round | Celtic | 4-1 |
| 2nd Round | Heart of Midlothian | 5-0 |
| 2nd Round | Aberdeen | 4-0 |
| 2nd Round | 0-1 | Motherwell |
| 2nd Round | Hibernian | 4-0 |
| 2nd Round | Kilmarnock | 1-0 |
| 2nd Round | 0-2 |
| 2nd Round | 0-3 | Rangers |
16th August 1988
| 2nd Round | 1-3 | St. Mirren |
| 2nd Round | 2-4 |
| 2nd Round | Livingston | 2-1 |
| 2nd Round | 0-2 | Dundee United |
11th August 1988
| 1st Round | 0-1 |
10th August 1988
| 1st Round | 0-0 |
| 1st Round | 3-1 |
| 1st Round | 2-4 |
| 1st Round | 1-2 |
| 1st Round | 3-0 |