| Final played at Hampden Park, Glasgow. | | date | Home | score | Away | HT | att. | | Sat 29.05.99 | Celtic FC | 0-1 | Rangers FC | | |
| date | Home | score | Away | HT | | | Round 1. | | Sat 05.12.98 | Arbroath FC | 1-2 | Partick Thistle | | | | Sat 05.12.98 | Dumbarton FC | 1-1 | Livingston FC | | | | Sat 05.12.98 | Queen's Park FC | 2-0 | Berwick Rangers | | | | Sat 05.12.98 | Stenhousemuir FC | 1-1 | Alloa Athletic | | | | Tue 08.12.98 | Livingston FC | 3-0 | Dumbarton FC | | | | Sat 12.12.98 | Alloa Athletic | 0-2 | Stenhousemuir FC | | | | Round 2. | | Sat 02.01.99 | Civil Service Strollers | 0-3 | Albion Rovers | | | | Sat 02.01.99 | Dalbeattie Star | 1-2 | East Stirlingshire FC | | | | Sat 02.01.99 | Forfar Athletic | 2-2 | East Fife FC | | | | Sat 02.01.99 | Huntly FC | 3-0 | Peterhead FC | | | | Sat 02.01.99 | Inverness CT | 1-2 | Livingston FC | | | | Sat 02.01.99 | Keith FC | 0-0 | Brechin City FC | 0-0 | | | Sat 02.01.99 | Montrose FC | 0-0 | Stirling Albion FC | 0-0 | | | Sat 02.01.99 | Partick Thistle | 5-2 | Cowdenbeath FC | | | | Sat 02.01.99 | Spartans FC | 1-1 | Clyde FC | | | | Sat 02.01.99 | Whitehill Welfare | 1-1 | Stenhousemuir FC | | | | Sat 09.01.99 | Queen Of The South | 1-3 | Ross County FC | | | | Mon 18.01.99 | Queen's Park FC | 1-1 | Clachnacuddin FC | | | | Wed 06.01.99 | Clyde FC | 5-0 | Spartans FC | | | | Sat 09.01.99 | Brechin City FC | 3-1 | Keith FC | | | | Sat 09.01.99 | East Fife FC | 0-1 | Forfar Athletic | | | | Sat 09.01.99 | Stenhousemuir FC | 2-0 | Whitehill Welfare | | | | Mon 18.01.99 | Stirling Albion FC | 2-1 | Montrose FC | | | | Sat 23.01.99 | Clachnacuddin FC | 2-3 | Queen's Park FC | | | | Round 3. | | Sat 23.01.99 | Aberdeen FC | 0-1 | Livingston FC | | | | Sat 23.01.99 | Ayr United | 3-0 | Kilmarnock FC | | | | Sat 23.01.99 | Brechin City FC | 1-1 | Albion Rovers | | | | Sat 23.01.99 | Celtic FC | 3-1 | Clydebank FC (old) | | | | Sat 23.01.99 | Falkirk FC | 3-0 | Huntly FC | | | | Sat 23.01.99 | Greenock Morton FC | 2-1 | Dundee FC | | | | Sat 23.01.99 | Hibernian FC | 1-1 | Stirling Albion FC | | | | Sat 23.01.99 | Partick Thistle | 1-2 | Dunfermline Athletic | | | | Sat 23.01.99 | Raith Rovers | 0-4 | Clyde FC | | | | Sat 23.01.99 | Rangers FC | 2-0 | Stenhousemuir FC | | | | Sat 23.01.99 | St. Johnstone FC | 1-0 | Forfar Athletic | | | | Sat 23.01.99 | St. Mirren FC | 1-1 | Hamilton Academical | | | | Sat 23.01.99 | Stranraer FC | 1-0 | East Stirlingshire FC | | | | Sun 24.01.99 | Motherwell FC | 3-1 | Heart of Midlothian | | | | Tue 02.02.99 | Queen's Park FC | 0-0 | Dundee United | 0-0 | | | Wed 03.02.99 | Clydebank FC | 1-1 | Ross County FC | | | | Tue 02.02.99 | Albion Rovers | 3-1 | Brechin City FC | | | | Tue 02.02.99 | Hamilton Academical | 1-0 | St. Mirren FC | | | | Tue 02.02.99 | Stirling Albion FC | 2-1 | Hibernian FC | | | | Tue 09.02.99 | Dundee United | 1-0 | Queen's Park FC | | | | Mon 15.02.99 | Ross County FC | 2-3 | Clydebank FC | | | | Round 16. | | Sat 13.02.99 | Ayr United | 1-0 | Albion Rovers | | | | Sat 13.02.99 | Celtic FC | 4-0 | Dunfermline Athletic | | | | Sat 13.02.99 | Greenock Morton FC | 6-1 | Clyde FC | | | | Sat 13.02.99 | Livingston FC | 1-3 | St. Johnstone FC | | | | Sat 13.02.99 | Motherwell FC | 2-0 | Stirling Albion FC | | | | Sat 13.02.99 | Stranraer FC | 1-2 | Falkirk FC | | | | Sun 14.02.99 | Hamilton Academical | 0-6 | Rangers FC | | | | Wed 03.03.99 | Clydebank FC | 2-2 | Dundee United | | | | Sat 06.03.99 | Dundee United | 3-0 | Clydebank FC | | | | Sat 06.03.99 | Motherwell FC | 0-2 | St. Johnstone FC | | | | Sun 07.03.99 | Rangers FC | 2-1 | Falkirk FC | | | | Mon 08.03.99 | Greenock Morton FC | 0-3 | Celtic FC | | | | Sat 13.03.99 | Ayr United | 0-0 | Dundee United | 0-0 | | | Wed 17.03.99 | Dundee United | 2-1 | Ayr United | | | | Sat 10.04.99 | Celtic FC | 2-0 | Dundee United | | | | Sat 10.04.99 | St. Johnstone FC | 0-4 | Rangers FC | | |
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Prepared and maintained by Todor Krastev
todor1966@yahoo.com
Last updated: 29 Jan 2022
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