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 Livingston 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 Livingston
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 Livingston
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 Livingston 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 Livingston
1st Round Arbroath 1-2 Partick Thistle