1. Round
09/12/2000 Stenhousemuir FC - Berwick Rangers 1:4
Whitehill Welfare - Peterhead FC 0:0
Albion Rovers - East Fife FC 1:1
Dumbarton FC - East Stirlingshire FC 1:1
12/12/2000 Brechin City FC - Forfar Athletic 3:0
18/12/2000 Queen Of The South - Clydebank FC 2:0
20/12/2000 Edinburgh City FC - Buckie Thistle 0:1
06/01/2001 Montrose FC - Arbroath FC 0:0
12/12/2000 East Fife FC - Albion Rovers 2:0
East Stirlingshire FC - Dumbarton FC 0:1
18/12/2000 Peterhead FC - Whitehill Welfare 3:0
09/01/2001 Arbroath FC - Montrose FC 1:2
2. Round
06/01/2001 The Spartans FC - Stirling Albion FC 1:3
Stranraer FC - Dumbarton FC 2:0
Berwick Rangers - Cowdenbeath FC 3:3
Buckie Thistle - Hamilton Academical 2:0
Peterhead FC - Cove Rangers 3:0
Coldstream FC - Brechin City FC 2:6
East Fife FC - Queen's Park FC 1:0
Partick Thistle - Deveronvale FC 3:0
13/01/2001 Montrose FC - Keith FC 1:1
27/01/2001 Elgin City - Queen Of The South 0:1
24/01/2001 Cowdenbeath FC - Berwick Rangers 0:1
Keith FC - Montrose FC 0:1 aet
3. Round
27/01/2001 St. Johnstone FC - Dunfermline Athletic 0:0
Berwick Rangers - Heart of Midlothian 0:0
Stirling Albion FC - Raith Rovers 2:0
Kilmarnock FC - Partick Thistle 1:0
Alloa Athletic - Aberdeen FC 0:3
Ross County FC - Buckie Thistle 2:1
Montrose FC - Dundee United 0:2
Inverness CT - Ayr United 4:3
Dundee FC - Falkirk FC 0:0
Hibernian FC - Clyde FC 6:1
Peterhead FC - Greenock Morton FC 4:1
East Fife FC - Livingston FC 1:4
Rangers FC - Brechin City FC 2:0
St. Mirren FC - Motherwell FC 1:2
28/01/2001 Stranraer FC - Celtic FC 1:4
12/02/2001 Queen Of The South - Clydebank FC (old) 1:3
07/02/2001 Heart of Midlothian - Berwick Rangers 2:1
12/02/2001 Falkirk FC - Dundee FC 0:2
13/02/2001 Dunfermline Athletic - St. Johnstone FC 3:2
Round of 16
17/02/2001 Heart of Midlothian - Dundee FC 1:1
Motherwell FC - Dundee United 0:2
Clydebank FC (old) - Peterhead FC dnp
Dunfermline Athletic - Celtic FC 2:2
Stirling Albion FC - Hibernian FC 2:3
Inverness CT - Kilmarnock FC 1:1
Livingston FC - Aberdeen FC 0:0
18/02/2001 Ross County FC - Rangers FC 2:3
06/03/2001 Kilmarnock FC - Inverness CT 2:1
Aberdeen FC - Livingston FC 0:1
07/03/2001 Celtic FC - Dunfermline Athletic 4:1
Dundee FC - Heart of Midlothian 0:1
Quarter-finals
10/03/2001 Kilmarnock FC - Hibernian FC 0:1
Livingston FC - Peterhead FC 3:1
11/03/2001 Celtic FC - Heart of Midlothian 1:0
Dundee United - Rangers FC 1:0
Semi-finals
14/04/2001 Hibernian FC - Livingston FC 3:0
15/04/2001 Celtic FC - Dundee United 3:1
Final
26/05/2001 Celtic FC - Hibernian FC 3:0 (1:0)