1. Round
11.12.1999
Hamilton Academical
Hamilton
Clyde FC
Clyde FC
Ended
Huntly FC
Huntly FC
East Stirling
East Stirlingshire FC
Ended
Total: 2:2
Ross County FC
Ross County
Forfar Athletic
Forfar Athletic
Ended
27.12.1999
Threave Rovers
Threave Rovers
Stenhousemuir
Stenhousemuir FC
Ended
1. Round Decider
03.01.2000
Forfar Athletic
Forfar Athletic
pso
Ross County
Ross County FC
Ended
2. Round
08.01.2000
Albion Rovers
Albion Rovers
Dalbeattie Star
Dalbeattie Star
Ended
Arbroath FC
Arbroath FC
Fraserburgh FC
Fraserburgh FC
Ended
Brechin City FC
Brechin City FC
Annan Athletic
Annan Athletic
Ended
Cowdenbeath FC
Cowdenbeath FC
Clyde FC
Clyde FC
Ended
Dumbarton FC
Dumbarton FC
Stenhousemuir
Stenhousemuir FC
Ended
Montrose FC
Montrose FC
Queen Of The South
Queen Of The South
Ended
Partick Thistle
Partick Thistle
East Stirling
East Stirlingshire FC
Ended
Peterhead FC
Peterhead
Forfar Athletic
Forfar Athletic
Ended
Queen's Park FC
Queen's Park FC
Berwick Rangers
Berwick Rangers
Ended
Stirling Albion FC
Stirling Albion
East Fife
East Fife FC
Ended
Stranraer FC
Stranraer FC
Clachnacuddin
Clachnacuddin FC
Ended
Whitehill Welfare
Whitehill Welfare
Alloa Ath.
Alloa Athletic
Ended
2. Round Repeat
15.01.2000
Annan Athletic
Annan Athletic
aet
Brechin City FC
Brechin City FC
Ended
Fraserburgh FC
Fraserburgh FC
Arbroath FC
Arbroath FC
Ended
19.01.2000
Dalbeattie Star
Dalbeattie Star
Albion Rovers
Albion Rovers
Ended
29.01.2000
Alloa Athletic
Alloa Ath.
Whitehill Welfare
Whitehill Welfare
Ended
3. Round
29.01.2000
Heart of Midlothian
Hearts FC
Stenhousemuir
Stenhousemuir FC
Ended
St. Mirren FC
St. Mirren
Aberdeen
Aberdeen FC
Ended
Albion Rovers
Albion Rovers
Partick Thistle
Partick Thistle
Ended
Falkirk FC
Falkirk
Peterhead
Peterhead FC
Ended
Arbroath FC
Arbroath FC
Motherwell
Motherwell FC
Ended
Queen Of The South
Queen Of The South
Livingston
Livingston FC
Ended
Clyde FC
Clyde FC
Raith Rovers
Raith Rovers
Ended
Stranraer FC
Stranraer FC
Berwick Rangers
Berwick Rangers
Ended
Clydebank FC
Clydebank FC
Stirling Albion
Stirling Albion FC
Ended
Hibernian FC
Hibernian FC
Dunfermline
Dunfermline Athletic
Ended
Dundee FC
Dundee FC
Ayr United
Ayr United
Ended
30.01.2000
St. Johnstone FC
St. Johnstone
Rangers FC
Rangers FC
Ended
Greenock Morton FC
Morton
Brechin City FC
Brechin City FC
Ended
Dundee United
Dundee Utd
Airdrieonians
Airdrieonians FC
Ended
05.02.2000
Kilmarnock FC
Kilmarnock
Alloa Ath.
Alloa Athletic
Ended
08.02.2000
Celtic FC
Celtic
Inverness
Inverness CT
Ended
3. Round Repeat
08.02.2000
Aberdeen FC
Aberdeen
St. Mirren
St. Mirren FC
Ended
Brechin City FC
Brechin City FC
pso
Morton
Greenock Morton FC
Ended
09.02.2000
Alloa Athletic
Alloa Ath.
Kilmarnock
Kilmarnock FC
Ended
15.02.2000
Ayr United
Ayr United
pso
Dundee FC
Dundee FC
Ended
19.02.2000
Motherwell FC
Motherwell
Arbroath FC
Arbroath FC
Ended
Round of 16
19.02.2000
Greenock Morton FC
Morton
Rangers FC
Rangers FC
Ended
Hibernian FC
Hibernian FC
Clydebank FC
Clydebank FC
Ended
Clyde FC
Clyde FC
Hearts FC
Heart of Midlothian
Ended
Berwick Rangers
Berwick Rangers
Falkirk
Falkirk FC
Ended
Alloa Athletic
Alloa Ath.
Dundee Utd
Dundee United
Ended
Partick Thistle
Partick Thistle
Livingston
Livingston FC
Ended
20.02.2000
Inverness CT
Inverness
Aberdeen
Aberdeen FC
Ended
26.02.2000
Motherwell FC
Motherwell
Ayr United
Ayr United
Ended
Round of 16 Repeat
22.02.2000
Dundee United
Dundee Utd
Alloa Ath.
Alloa Athletic
Ended
29.02.2000
Falkirk FC
Falkirk
Berwick Rangers
Berwick Rangers
Ended
Clydebank FC
Clydebank FC
Hibernian FC
Hibernian FC
Ended
Aberdeen FC
Aberdeen
Inverness
Inverness CT
Ended
Quarter-finals
11.03.2000
Ayr United
Ayr United
Partick Thistle
Partick Thistle
Ended
Hibernian FC
Hibernian FC
Falkirk
Falkirk FC
Ended
12.03.2000
Rangers FC
Rangers FC
Hearts FC
Heart of Midlothian
Ended
Dundee United
Dundee Utd
Aberdeen
Aberdeen FC
Ended
Semi-finals
08.04.2000
Ayr United
Ayr United
Rangers FC
Rangers FC
Ended
Hibernian FC
Hibernian FC
Aberdeen
Aberdeen FC
Ended
Final
27.05.2000
Rangers FC
Rangers FC
Aberdeen
Aberdeen FC
Ended
