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FinalFansPenETScore- 1990-05-12Aberdeen Celtic 60' 4939:80:00:0 (0:0)
1/2Fans Score- 1990-04-14Celtic Clydebank 34' 768 2:0 (1:0)
- Aberdeen Dundee United 16' 581 4:0 (2:0)
1/4ReplayFans Score- 1990-03-21Stirling Albion FCClydebank 3' 738 0:1 (0:0)
- Celtic Dunfermline Athletic 40' 798 3:0 (2:0)
Fans Score- 1990-03-17Dunfermline Athletic Celtic 19' 568 0:0 (0:0)
- Clydebank Stirling Albion FC2' 595 1:1 (1:0)
- Dundee United Hibernian 13' 847 1:0 (1:0)
- Aberdeen Heart of Midlothian 22' 500 4:1 (1:1)
1/8ReplayFans Score- 1990-03-12Clydebank Saint Mirren 6' 333 3:2 (2:2)
Fans Score- 1990-02-28Saint Mirren Clydebank 5' 800 1:1 (0:0)
- Stirling Albion FCInverness Caled. Th. 3' 495 6:2 (3:2)
- 1990-02-27Cowenbeath Dunfermline Athletic 8' 500 1:2 (0:1)
- 1990-02-26Dundee United Queen of the South 5' 948 2:1 (1:1)
- 1990-02-25Celtic Rangers 52' 565 1:0 (1:0)
- 1990-02-24Heart of Midlothian Motherwell 19' 161 4:0 (3:0)
- Hibernian East Fife 7' 232 5:1 (3:0)
- Aberdeen Morton 14' 500 2:1 (0:1)
1/16ReplayFans Score- 1990-01-31Hamilton Academical Dunfermline Athletic 4' 200 0:1 (0:1)
- 1990-01-29Alloa Athletic Queen of the South 1' 073 0:12:2 (2:1)
- Raith Rovers Morton 2' 740 1:3 (1:1)
- 1990-01-24Inverness Caled. Th. Airdrieonians FC3' 2005:40:01:1 (1:1)
- Saint Mirren Ayr United 5' 413 2:1 (2:0)
- 1990-01-23Dundee United Dundee FC15' 503 1:0 (0:0)
Fans Score- 1990-01-29East Stirlingshire FCStirling Albion FC527 0:1 (0:1)
- 1990-01-20Dundee FCDundee United 14' 276 0:0 (0:0)
- Albion Rovers Clydebank 984 0:2 (0:0)
- Brechin City Hibernian 3' 007 0:2 (0:0)
- Dunfermline Athletic Hamilton Academical 6' 439 0:0 (0:0)
- Heart of Midlothian Falkirk 14' 259 2:0 (0:0)
- Ayr United Saint Mirren 7' 869 0:0 (0:0)
- Queen of the South Alloa Athletic 1' 100 0:0 (0:0)
- Cowenbeath Stranraer 587 3:1 (1:0)
- Airdrieonians FCInverness Caled. Th. 2' 516 2:2 (1:0)
- Rangers Saint Johnstone 39' 003 3:0 (1:0)
- Motherwell Clyde 4' 077 7:0 (2:0)
- East Fife Livingston 1' 100 3:1 (1:1)
- Forfar Ath Celtic 8' 388 1:2 (1:1)
- Morton Raith Rovers 3' 100 2:2 (0:2)
- Partick Thistle Aberdeen 11' 875 2:6 (2:2)
Round 2ReplayFansPenETScore- 1990-01-06Kilmarnock Stranraer 5' 0333:40:00:0 (0:0)
- Brechin City Elgin City 1' 500 8:0 (2:0)
- Inverness Caled. Th. Gala Fairydean Rovers1' 595 4:1 (1:1)
Fans Score- 1990-01-07Ross County East Fife 1' 750 1:4 (1:1)
- 1989-12-30Stenhousemuir Queen of the South 750 0:1 (0:0)
- Stranraer Kilmarnock 3' 600 1:1 (1:0)
- Stirling Albion FCWhitehill Welfare 583 3:0 (1:0)
- Elgin City Brechin City 3' 370 2:2 (0:1)
- Dumbarton Cowenbeath 700 0:2 (0:1)
- Vale of Leithen East Stirlingshire FC350 1:3 (1:1)
- Gala Fairydean RoversInverness Caled. Th. 650 2:2 (1:1)
Round 1ReplayFans Score- 1989-12-12Stenhousemuir Berwick Rangers 500 1:0 (0:0)
Fans Score- 1989-12-09Stirling Albion FCColdstream FC500 4:0 (0:0)
- Queen of the South Cove Rangers 870 2:1 (0:0)
- Brechin City Montrose 630 3:1 (0:0)
- Queen's Park Dumbarton 784 1:2 (0:1)
- Berwick Rangers Stenhousemuir 300 1:1 (1:1)
- Elgin City Arbroath 1' 542 2:1 (1:1)
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