29th November 1998
| Final | Rangers | 2-1 |
27th October 1998
| Semi Final | 3-0 | Heart of Midlothian |
25th October 1998
| Semi Final | Rangers | 5-0 |
9th September 1998
| Quarter Final | Heart of Midlothian | 1-1 |
8th September 1998
| Quarter Final | 4-0 | Hibernian |
| Quarter Final | Kilmarnock | 0-1 |
| Quarter Final | 0-2 | Rangers |
19th August 1998
| 3rd Round | 2-0 | Dundee United |
| 3rd Round | Hibernian | 1-0 | Aberdeen |
| 3rd Round | Heart of Midlothian | 4-2 |
| 3rd Round | 1-0 | Celtic |
18th August 1998
| 3rd Round | Rangers | 4-0 |
| 3rd Round | Motherwell | 0-2 |
| 3rd Round | Kilmarnock | 3-1 | Livingston |
| 3rd Round | 0-1 |
8th August 1998
| 2nd Round | 0-2 |
| 2nd Round | St. Mirren | 1-3 |
| 2nd Round | 3-0 |
| 2nd Round | 2-0 |
| 2nd Round | 0-1 |
| 2nd Round | Livingston | 1-0 |
| 2nd Round | 0-3 | Aberdeen |
| 2nd Round | 1-2 | Hibernian |
| 2nd Round | 0-1 | Motherwell |
| 2nd Round | Dundee United | 2-2 |
| 2nd Round | 0-1 |
| 2nd Round | 1-5 |
1st August 1998
| 1st Round | 1-1 |
| 1st Round | 1-0 |
| 1st Round | 4-1 |
| 1st Round | 1-3 |
| 1st Round | 1-4 |
| 1st Round | 0-1 |
| 1st Round | 3-2 |
| 1st Round | 0-4 |
| 1st Round | 0-2 | Livingston |
| 1st Round | 1-1 |
| 1st Round | 2-2 |
| 1st Round | 0-1 |