1st Round (3 Dec 1988):
Berwick Rangers 1-1 Alloa Athletic
East Fife 4-1 Spartans
E.Stirlingshire 1-0 Gala Fairydean
Inverness Thistle 0-0 Dumbarton
Montrose 2-0 Arbroath
Stranraer 2-2 Stirling Albion
Replays 1st Round (10 Dec 1988):
Alloa Athletic 2-1 (7 Dec) Berwick Rangers
Dumbarton 2-1 Inverness Thistle
Stirling Albion 0-1 Stranraer
Bye: 10 clubs.
2nd Round (7 Jan 1989):
Annan Athletic 1-5 Queen's Park
Coldstream 1-1 Albion Rovers
Cowdenbeath 1-1 Stenhousemuir
E.Stirlingshire 1-2 Montrose
Elgin City 2-2 Dumbarton
Forres Mechanics 1-1 Alloa Athletic
Inverness Caledonian 1-1 Brechin City
Stranraer 2-1 East Fife
Replays 2nd Round (14 Jan 1989):
Albion Rovers 1-0 Coldstream
Alloa Athletic 2-0 Forres Mechanics
Brechin City 2-1 Inverness Caledonian
Dumbarton 4-0 Elgin City
Stenhousemuir 3-2 Cowdenbeath
Clubs from Premier (10) and First Division (14) are added.
3rd Round (28 Jan 1989):
Alloa Athletic 3-1 Albion Rovers
Celtic 2-0 Dumbarton
Clydebank 2-1 Montrose
Dundee FC 1-2 Dundee United
Dunfermline Athletic 0-0 Aberdeen
Falkirk 1-1 Motherwell
Forfar Athletic 1-1 Clyde
Heart of Midlothian 4-1 Ayr United
Hibernian 1-0 Brechin City
Meadowbank Thistle 2-0 (29 Jan) Hamilton Academical
Greenock Morton 0-0 Airdrieonians
Partick Thistle 0-0 St Mirren
Queen of the South 2-2 Kilmarnock
Queen's Park 0-0 Stranraer
Raith Rovers 1-1 Rangers
St.Johnstone 2-0 Stenhousemuir
Replays 3rd Round (1 Feb 1989):
Aberdeen 3-1 Dunfermline Athletic
Airdrieonians – Greenock Morton 0-1
Clyde 0-1 Forfar Athletic (31 Jan)
Kilmarnock 0-1 Queen of the South
Motherwell 2-1 Falkirk
Rangers 3-0 Raith Rovers
St Mirren 1-3 Partick Thistle (31 Jan)
Stranraer 1-0 Queen's Park
4th Round (18 Feb 1989):
Aberdeen 1-1 Dundee United
Celtic 4-1 Clydebank
Heart of Midlothian 2-0 Partick Thistle
Hibernian 2-1 Motherwell
Meadowbank Thistle 0-1 Greenock Morton
Queen of the South 0-0 Alloa Athletic
Rangers 8-0 Stranraer
St.Johnstone 2-1 Forfar Athletic
Replays 4th Round (22 Feb 1989):
Alloa Athletic 4-2 Queen of the South
Dundee United 1-1 Aberdeen aet
2nd Replay 4th Round (27 Feb 1989):
Dundee United 1-0 Aberdeen
Quarter Finals (18-22 March 1989):
Celtic 2-1 Heart of Midlothian
Hibernian 1-0 Alloa Athletic
Greenock Morton 2-2 St.Johnstone
Rangers 2-2 Dundee United
Replay Quarter Finals (27 Mar 1989):
Dundee United 0-1 Rangers
St.Johnstone 3-2 Greenock Morton
Semi Finals (15/16 Apr 1989):
Celtic 3-1 Hibernian Hampden Park, Glasgow.
Rangers 0-0 St.Johnstone Celtic Park, Glasgow
Replay Semi Finals (18 Apr 1989):
Rangers – St.Johnstone 4-0 Celtic Park, Glasgow.
Final (Hampden Park, Glasgow, 20 May 1989):
Celtic – Rangers 1-0
Cup Winners: Celtic.