29th May 1999
| Final | Rangers | 1-0 | Celtic |
11th April 1999
| Semi Final | St. Johnstone | 0-4 | Rangers |
10th April 1999
| Semi Final | Celtic | 2-0 | Dundee United |
16th March 1999
| 5th Round Replay | Dundee United | 2-1 | Ayr United |
13th March 1999
| 5th Round | Ayr United | 0-0 | Dundee United |
8th March 1999
| 5th Round | Greenock Morton | 0-3 | Celtic |
7th March 1999
| 5th Round | Rangers | 2-1 | Falkirk |
6th March 1999
| 5th Round | Motherwell | 0-2 | St. Johnstone |
| 4th Round Replay | Dundee United | 3-0 |
3rd March 1999
| 4th Round | 2-2 | Dundee United |
15th February 1999
| 3rd Round Replay | Ross County | 2-3 |
14th February 1999
| 4th Round | 0-6 | Rangers |
13th February 1999
| 4th Round | Stranraer | 1-2 | Falkirk |
| 4th Round | Motherwell | 2-0 | Stirling Albion |
| 4th Round | Greenock Morton | 6-1 | Clyde |
| 4th Round | 1-3 | St. Johnstone |
| 4th Round | Celtic | 4-0 | Dunfermline Athletic |
| 4th Round | Ayr United | 1-0 | Albion Rovers |
9th February 1999
| 3rd Round Replay | Dundee United | 1-0 | Queen's Park |
3rd February 1999
| 3rd Round | 1-1 | Ross County |
2nd February 1999
| 3rd Round Replay | Stirling Albion | 2-1 | Hibernian |
| 3rd Round | Queen's Park | 0-0 | Dundee United |
| 3rd Round Replay | 1-0 | St. Mirren |
| 3rd Round Replay | Albion Rovers | 3-1 | Brechin City |
24th January 1999
| 3rd Round | Motherwell | 3-1 | Heart of Midlothian |
23rd January 1999
| 3rd Round | Stranraer | 1-0 |
| 3rd Round | St. Mirren | 1-1 |
| 3rd Round | St. Johnstone | 1-0 | Forfar Athletic |
| 3rd Round | Rangers | 2-0 | Stenhousemuir |
| 3rd Round | Raith Rovers | 0-4 | Clyde |
| 3rd Round | Partick Thistle | 1-2 | Dunfermline Athletic |
| 3rd Round | Greenock Morton | 2-1 | Dundee |
| 3rd Round | Hibernian | 1-1 | Stirling Albion |
| 3rd Round | Falkirk | 3-0 |
| 3rd Round | Celtic | 3-1 | Airdrie United |
| 3rd Round | Brechin City | 1-1 | Albion Rovers |
| 3rd Round | Ayr United | 3-0 | Kilmarnock |
| 3rd Round | Aberdeen | 0-1 |
| 2nd Round Replay | 2-3 | Queen's Park |
18th January 1999
| 2nd Round Replay | Stirling Albion | 2-1 | Montrose |
| 2nd Round | Queen's Park | 1-1 |
9th January 1999
| 2nd Round | Queen of the South | 1-3 | Ross County |
| 2nd Round Replay | Brechin City | 3-1 |
6th January 1999
| 2nd Round Replay | Stenhousemuir | 2-0 |
| 2nd Round Replay | East Fife | 0-1 | Forfar Athletic |
| 2nd Round Replay | Clyde | 5-0 |
2nd January 1999
| 2nd Round | 1-1 | Stenhousemuir |
| 2nd Round | 1-1 | Clyde |
| 2nd Round | Partick Thistle | 5-2 | Cowdenbeath |
| 2nd Round | Montrose | 0-0 | Stirling Albion |
| 2nd Round | 0-0 | Brechin City |
| 2nd Round | Inverness Caledonian Thistle | 1-2 |
| 2nd Round | 3-0 | Peterhead |
| 2nd Round | Forfar Athletic | 2-2 | East Fife |
| 2nd Round | 1-2 |
| 2nd Round | 0-3 | Albion Rovers |
12th December 1998
| 1st Round Replay | Alloa Athletic | 0-2 | Stenhousemuir |
8th December 1998
| 1st Round Replay | 3-0 | Dumbarton |
5th December 1998
| 1st Round | Stenhousemuir | 1-1 | Alloa Athletic |
| 1st Round | Queen's Park | 2-0 |
| 1st Round | Dumbarton | 1-1 |
| 1st Round | Arbroath | 1-2 | Partick Thistle |