1. Round
27/09/2008 15:00 Lochee United FC - Bathgate Thistle FC 3:1
15:00 Selkirk FC - Coldstream FC 1:1
15:00 St. Cuthbert Wanderers - Wick Academy FC 0:3
15:00 Fraserburgh FC - Hawick Royal Albert 6:3
15:00 Newton Stewart FC - Brora Rangers FC 1:1
15:00 Huntly FC - Girvan FC 1:0
15:00 Pollok FC - Spartans FC 1:1
15:00 Edinburgh City FC - Nairn County FC 2:0
15:00 Inverurie Loco Works - Deveronvale FC 5:2
15:00 Dalbeattie Star - Lossiemouth FC 5:1
15:00 Edinburgh University AFC - Civil Service Strollers 1:2
15:00 Preston Athletic FC - Gala Fairydean 3:1
15:00 Wigtown & Bladnoch - Forres Mechanics FC 2:2
15:00 Clachnacuddin FC - Burntisland Shipyard 4:0
15:00 Glasgow University - Vale of Leithen FC 0:1
15:00 Rothes FC - Buckie Thistle 1:3
15:00 Golspie Sutherland - Threave Rovers 0:3
15:00 Banks O' Dee FC - Fort William FC 10:0
04/10/2008 15:00 Coldstream FC - Selkirk FC 2:3 pso
15:00 Brora Rangers FC - Newton Stewart FC 2:1 aet
15:00 Spartans FC - Pollok FC 1:0
15:00 Forres Mechanics FC - Wigtown & Bladnoch 2:0
2. Round
25/10/2008 14:30 Lochee United FC - Buckie Thistle 3:0
15:00 Clachnacuddin FC - Crichton FC 1:0
15:00 Edinburgh City FC - Wick Academy FC 0:0
15:00 Cove Rangers - Whitehill Welfare 1:0
15:00 Dalbeattie Star - Selkirk FC 6:0
15:00 Montrose FC - Huntly FC 2:0
15:00 Fraserburgh FC - Dumbarton FC 0:1
15:00 Berwick Rangers - Albion Rovers 1:2
15:00 Inverurie Loco Works - Banks O' Dee FC 5:1
15:00 Stenhousemuir FC - Threave Rovers 5:0
15:00 Brora Rangers FC - Forfar Athletic 1:3
15:00 Cowdenbeath FC - Elgin City 1:2
15:00 Forres Mechanics FC - Keith FC 1:1
26/10/2008 15:00 East Stirlingshire FC - Preston Athletic FC 4:2
01/11/2008 15:00 Civil Service Strollers - Vale of Leithen FC 0:1
15:00 Annan Athletic - Spartans FC 1:2
15:00 Keith FC - Forres Mechanics FC 0:3 pso
15:00 Wick Academy FC - Edinburgh City FC 1:4
3. Round
29/11/2008 15:00 Stirling Albion FC - Partick Thistle 2:3
15:00 East Stirlingshire FC - Livingston FC 2:1
15:00 Albion Rovers - Queen's Park FC 1:2
15:00 East Fife FC - Arbroath FC 2:0
15:00 Peterhead FC - Greenock Morton FC 2:1
15:00 Clyde FC - Montrose FC 2:0
15:00 Airdrie United FC - Cove Rangers 3:0
15:00 Raith Rovers - Alloa Athletic 0:0
15:00 Clachnacuddin FC - Stenhousemuir FC 0:5
15:00 Ross County FC - Dumbarton FC 2:2
06/12/2008 15:00 Forres Mechanics FC - Dalbeattie Star 2:2
08/12/2008 19:45 Edinburgh City FC - Brechin City FC 0:3
13/12/2008 15:00 Inverurie Loco Works - Vale of Leithen FC 4:0
15/12/2008 19:45 Forfar Athletic - Stranraer FC 2:0
19:45 Elgin City - Spartans FC 1:2
17/12/2008 13:45 Lochee United FC - Ayr United 1:1
09/12/2008 19:45 Alloa Athletic - Raith Rovers 2:1
15/12/2008 13:00 Dalbeattie Star - Forres Mechanics FC 2:4 aet
19:45 Dumbarton FC - Ross County FC 1:2
23/12/2008 19:45 Ayr United - Lochee United FC 3:1
4. Round
10/01/2009 15:00 Peterhead FC - Queen's Park FC 2:2
15:00 Alloa Athletic - Aberdeen FC 1:2
15:00 Falkirk FC - Queen Of The South 4:2
15:00 Airdrie United FC - Spartans FC 2:1
15:00 Ross County FC - Hamilton Academical 0:1
15:00 Inverness CT - Partick Thistle 3:0
15:00 Celtic FC - Dundee FC 2:1
15:00 Stenhousemuir FC - East Fife FC 0:1
15:00 Ayr United - Kilmarnock FC 2:2
15:00 Dunfermline Athletic - Clyde FC 2:0
11/01/2009 12:15 Hibernian FC - Heart of Midlothian 0:2
15:00 East Stirlingshire FC - Dundee United 0:4
13/01/2009 19:45 Brechin City FC - St. Mirren FC 1:3
19:45 Forfar Athletic - Forres Mechanics FC 6:1
20:05 St. Johnstone FC - Rangers FC 0:2
02/02/2009 19:45 Inverurie Loco Works - Motherwell FC 0:3
20/01/2009 19:45 Queen's Park FC - Peterhead FC 1:0
22/01/2009 19:30 Kilmarnock FC - Ayr United 3:1
Round of 16
07/02/2009 15:00 Heart of Midlothian - Falkirk FC 0:1
15:00 Motherwell FC - St. Mirren FC 1:1
15:00 Celtic FC - Queen's Park FC 2:1
15:00 Hamilton Academical - Dundee United 2:1
15:00 Inverness CT - Kilmarnock FC 2:0
17/02/2009 19:45 Airdrie United FC - Dunfermline Athletic 1:2
19:45 Aberdeen FC - East Fife FC 5:0
18/02/2009 19:45 Forfar Athletic - Rangers FC 0:4
19/02/2009 19:45 St. Mirren FC - Motherwell FC 1:0
Quarter-finals
07/03/2009 12:15 St. Mirren FC - Celtic FC 1:0
15:00 Dunfermline Athletic - Aberdeen FC 1:1
15:00 Inverness CT - Falkirk FC 0:1
08/03/2009 15:00 Rangers FC - Hamilton Academical 5:1
18/03/2009 19:45 Aberdeen FC - Dunfermline Athletic 2:4 pso
Semi-finals
25/04/2009 12:15 Rangers FC - St. Mirren FC 3:0 (1:0)
26/04/2009 15:00 Falkirk FC - Dunfermline Athletic 2:0 (0:0)
Final
30/05/2009 15:00 Falkirk FC - Rangers FC 0:1 (0:0)