| Matches: 1968 – 1969 | Match Pictures: 1968-69 | Scottish Cup |
1st Preliminary (14 Dec 1968):
Alloa Athletic 6-1 Ross County
Brechin City 1-1 Montrose
Cowdenbeath 1-0 Clydebank
Forfar Athletic 1-2 Nairn County
St.Cuthbert Wanderers 1-0 Civil Service Strollers
Replay 1st Preliminary:
Montrose 3-2 (18 Dec) Brechin City
Bye: 11 clubs.
2nd Preliminary (4 January 1969):
Alloa Athletic 0-0 E.Stirlingshire
Dumbarton 3-2 Vale of Leithen
Glasgow University 5-2 St.Cuthbert Wanderers
Hamilton Academical 0-2 Cowdenbeath
Montrose 6-1 Fraserburgh
Nairn County 0-2 Berwick Rangers
Stenhousemuir 1-0 Albion Rovers
Stranraer 2-0 Elgin City
Replay 2nd Preliminary (8 Jan 1969):
E.Stirlingshire 2-1 Alloa Athletic
The 18 clubs from Division 1 and remaining 6 clubs from Division 2 are added.
1st Round (25 January 1969):
Aberdeen 3-0 Berwick Rangers
Ayr United 1-0 Queen of the South
Dumbarton 0-1 St Mirren
Dundee FC 1-2 Heart of Midlothian
Dundee United 2-1 Queen's Park
E.Stirlingshire 2-0 Stirling Albion
Falkirk 1-2 Greenock Morton
Kilmarnock 6-0 Glasgow University
Montrose 1-0 Cowdenbeath
Motherwell 1-1 Clyde
Partick Thistle 3-3 Celtic
Raith Rovers 0-2 Dunfermline Athletic
Rangers 1-0 Hibernian
St.Johnstone 3-2 Arbroath
Stenhousemuir 0-3 Airdrieonians
Stranraer 3-1 East Fife Methil
Replays 1st Round (29 Jan 1969):
Celtic 8-1 Partick Thistle
Clyde 2-1 (28 Jan) Motherwell
2nd Round (8 February 1969):
Aberdeen 2-2 (25 Feb) Dunfermline Athletic
Airdrieonians 1-1 (12 Feb) St Mirren
Clyde 0-0 (12 Feb) Celtic
Dundee United 6-2 Ayr United
E.Stirlingshire 1-1 St.Johnstone
Montrose 1-1 Kilmarnock
Rangers 2-0 (24 Feb) Heart of Midlothian
Stranraer 1-3 Greenock Morton
Replays 2nd Round (24 February 1969):
Celtic 3-0 Clyde
Dunfermline Athletic 0-2 (26 Feb) Aberdeen
Kilmarnock 4-1 (12 Feb) Montrose
St.Johnstone 3-0 E.Stirlingshire
St Mirren 1-3 Airdrieonians
Quarter Finals (1 March 1969):
Aberdeen 0-0 Kilmarnock
Celtic 3-2 St.Johnstone
Dundee United 2-3 Greenock Morton
Rangers 1-0 Airdrieonians
Replay Quarter Finals:
Kilmarnock 0-3 (5 Mar) Aberdeen
Semi Finals (22 March 1969):
Celtic 4-1 Greenock Morton Hampden Park, Glasgow
Rangers 6-1 Aberdeen Celtic Park, Glasgow
Final (Hampden Park, 26 April 1969):
Celtic 4-0 Rangers
Cup Winners: Celtic.