18th May 1991
| Final | Motherwell | 4-3 | Dundee United |
9th April 1991
| Semi Final Replay | Motherwell | 4-2 | Celtic |
6th April 1991
| Semi Final | Dundee United | 2-1 |
3rd April 1991
| Semi Final | Motherwell | 0-0 | Celtic |
19th March 1991
| 5th Round Replay | 1-1 | Motherwell |
17th March 1991
| 5th Round | Celtic | 2-0 | Rangers |
16th March 1991
| 5th Round | Motherwell | 0-0 |
| 5th Round | 5-2 |
13th March 1991
| 5th Round | Dundee United | 3-1 |
2nd March 1991
| 4th Round | 3-0 | Livingston |
27th February 1991
| 4th Round Replay | 2-3 |
26th February 1991
| 4th Round | Celtic | 3-0 | St. Mirren |
23rd February 1991
| 4th Round | 0-0 |
| 4th Round | 2-0 | Kilmarnock |
| 4th Round | Motherwell | 4-2 |
| 4th Round | Rangers | 5-0 |
| 4th Round | 2-1 | Hibernian |
| 3rd Round | 1-6 | Livingston |
| 4th Round | Dundee United | 2-0 |
30th January 1991
| 3rd Round Replay | 3-4 |
| 3rd Round Replay | 4-3 |
29th January 1991
| 3rd Round | Rangers | 2-0 |
| 3rd Round Replay | Dundee United | 2-1 |
28th January 1991
| 3rd Round | 0-2 | Hibernian |
| 2nd Round Replay | 2-6 |
26th January 1991
| 3rd Round | 0-2 | Celtic |
| 3rd Round | 1-1 | Dundee United |
| 3rd Round | 1-0 |
| 3rd Round | 0-0 |
| 3rd Round | 0-1 |
| 3rd Round | 2-1 | Heart of Midlothian |
| 3rd Round | Aberdeen | 0-1 | Motherwell |
| 3rd Round | 1-2 |
| 3rd Round | 1-5 | St. Mirren |
| 3rd Round | 0-1 |
| 3rd Round | 0-1 |
| 3rd Round | 0-0 |
| 3rd Round | Kilmarnock | 3-2 |
23rd January 1991
| 2nd Round | 2-2 |
21st January 1991
| 2nd Round Replay | 2-0 |
9th January 1991
| 2nd Round | 0-0 |
7th January 1991
| 2nd Round Replay | 1-0 |
5th January 1991
| 2nd Round | 1-1 |
29th December 1990
| 2nd Round | 1-0 |
| 2nd Round | 1-4 |
| 2nd Round | 0-2 |
| 2nd Round | 1-2 |
| 2nd Round | 2-0 |
17th December 1990
| 1st Round Replay | 1-4 |
15th December 1990
| 1st Round Replay | 1-3 |
| 1st Round | 1-2 |
| 1st Round | 0-4 |
11th December 1990
| 1st Round | 0-0 |
8th December 1990
| 1st Round | 1-3 |
| 1st Round | 3-1 |
| 1st Round | 1-1 |