29th May 1999
| Final | Rangers | 1-0 | Celtic |
11th April 1999
| Semi Final | 0-4 | Rangers |
10th April 1999
| Semi Final | Celtic | 2-0 | Dundee United |
16th March 1999
| 5th Round Replay | Dundee United | 2-1 |
13th March 1999
| 5th Round | 0-0 | Dundee United |
8th March 1999
| 5th Round | 0-3 | Celtic |
7th March 1999
| 5th Round | Rangers | 2-1 |
6th March 1999
| 5th Round | Motherwell | 0-2 |
| 4th Round Replay | Dundee United | 3-0 |
3rd March 1999
| 4th Round | 2-2 | Dundee United |
15th February 1999
| 3rd Round Replay | 2-3 |
14th February 1999
| 4th Round | 0-6 | Rangers |
13th February 1999
| 4th Round | 1-2 |
| 4th Round | Motherwell | 2-0 |
| 4th Round | 6-1 |
| 4th Round | Livingston | 1-3 |
| 4th Round | Celtic | 4-0 |
| 4th Round | 1-0 |
9th February 1999
| 3rd Round Replay | Dundee United | 1-0 |
3rd February 1999
| 3rd Round | 1-1 |
2nd February 1999
| 3rd Round Replay | 2-1 | Hibernian |
| 3rd Round | 0-0 | Dundee United |
| 3rd Round Replay | 1-0 | St. Mirren |
| 3rd Round Replay | 3-1 |
24th January 1999
| 3rd Round | Motherwell | 3-1 | Heart of Midlothian |
23rd January 1999
| 3rd Round | 1-0 |
| 3rd Round | St. Mirren | 1-1 |
| 3rd Round | 1-0 |
| 3rd Round | Rangers | 2-0 |
| 3rd Round | 0-4 |
| 3rd Round | 1-2 |
| 3rd Round | 2-1 |
| 3rd Round | Hibernian | 1-1 |
| 3rd Round | 3-0 |
| 3rd Round | Celtic | 3-1 |
| 3rd Round | 1-1 |
| 3rd Round | 3-0 | Kilmarnock |
| 3rd Round | Aberdeen | 0-1 | Livingston |
| 2nd Round Replay | 2-3 |
18th January 1999
| 2nd Round Replay | 2-1 |
| 2nd Round | 1-1 |
9th January 1999
| 2nd Round | 1-3 |
| 2nd Round Replay | 3-1 |
6th January 1999
| 2nd Round Replay | 2-0 |
| 2nd Round Replay | 0-1 |
| 2nd Round Replay | 5-0 |
2nd January 1999
| 2nd Round | 1-1 |
| 2nd Round | 1-1 |
| 2nd Round | 5-2 |
| 2nd Round | 0-0 |
| 2nd Round | 0-0 |
| 2nd Round | 1-2 | Livingston |
| 2nd Round | 3-0 |
| 2nd Round | 2-2 |
| 2nd Round | 1-2 |
| 2nd Round | 0-3 |
12th December 1998
| 1st Round Replay | 0-2 |
8th December 1998
| 1st Round Replay | Livingston | 3-0 |
5th December 1998
| 1st Round | 1-1 |
| 1st Round | 2-0 |
| 1st Round | 1-1 | Livingston |
| 1st Round | 1-2 |