29th November 1998
| Final | Rangers | 2-1 | St. Johnstone |
27th October 1998
| Semi Final | St. Johnstone | 3-0 | Heart of Midlothian |
25th October 1998
| Semi Final | Rangers | 5-0 | Airdrie United |
9th September 1998
| Quarter Final | Heart of Midlothian | 1-1 | Ross County |
8th September 1998
| Quarter Final | St. Johnstone | 4-0 | Hibernian |
| Quarter Final | Kilmarnock | 0-1 | Airdrie United |
| Quarter Final | Ayr United | 0-2 | Rangers |
19th August 1998
| 3rd Round | Ross County | 2-0 | Dundee United |
| 3rd Round | Hibernian | 1-0 | Aberdeen |
| 3rd Round | Heart of Midlothian | 4-2 | Raith Rovers |
| 3rd Round | Airdrie United | 1-0 | Celtic |
18th August 1998
| 3rd Round | Rangers | 4-0 | Alloa Athletic |
| 3rd Round | Motherwell | 0-2 | Ayr United |
| 3rd Round | Kilmarnock | 3-1 |
| 3rd Round | Falkirk | 0-1 | St. Johnstone |
8th August 1998
| 2nd Round | Stenhousemuir | 0-2 | Airdrie United |
| 2nd Round | St. Mirren | 1-3 | Ayr United |
| 2nd Round | St. Johnstone | 3-0 | Stranraer |
| 2nd Round | Raith Rovers | 2-0 |
| 2nd Round | Greenock Morton | 0-1 | Ross County |
| 2nd Round | 1-0 | Dunfermline Athletic |
| 2nd Round | Inverness Caledonian Thistle | 0-3 | Aberdeen |
| 2nd Round | 1-2 | Hibernian |
| 2nd Round | East Fife | 0-1 | Motherwell |
| 2nd Round | Dundee United | 2-2 | Stirling Albion |
| 2nd Round | Dundee | 0-1 | Alloa Athletic |
| 2nd Round | 1-5 | Falkirk |
1st August 1998
| 1st Round | Stranraer | 1-1 | Albion Rovers |
| 1st Round | Stenhousemuir | 1-0 |
| 1st Round | Ross County | 4-1 | Montrose |
| 1st Round | Queen's Park | 1-3 | Ayr United |
| 1st Round | Queen of the South | 1-4 | Inverness Caledonian Thistle |
| 1st Round | Forfar Athletic | 0-1 | Stirling Albion |
| 1st Round | East Fife | 3-2 | Partick Thistle |
| 1st Round | Dumbarton | 0-4 | Alloa Athletic |
| 1st Round | Cowdenbeath | 0-2 |
| 1st Round | Clyde | 1-1 |
| 1st Round | Brechin City | 2-2 |
| 1st Round | Arbroath | 0-1 |