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FinalFans Score- 1999-05-29Rangers Celtic 52' 670 1:0 (0:0)
1/2Fans Score- 1999-04-11Rangers Saint Johnstone 20' 664 4:0 (2:0)
- 1999-04-10Celtic Dundee United 43' 491 2:0 (2:0)
1/4ReplayFans Score- 1999-03-17Dundee United Ayr United 7' 313 2:1 (1:0)
Fans Score- 1999-03-13Ayr United Dundee United 5' 508 0:0 (0:0)
- 1999-03-08Morton Celtic 12' 062 0:3 (0:1)
- 1999-03-07Rangers Falkirk 39' 250 2:1 (0:0)
- 1999-03-06Motherwell Saint Johnstone 7' 660 0:2 (0:0)
1/8ReplayFans Score- 1999-03-06Dundee United Clydebank 5' 570 3:0 (1:0)
Fans Score- 1999-03-03Clydebank Dundee United 320 2:2 (1:0)
- 1999-02-14Hamilton Academical Rangers 7' 339 0:6 (0:2)
- 1999-02-13Motherwell Stirling Albion FC7' 244 2:0 (0:0)
- Ayr United Albion Rovers 3' 229 1:0 (0:0)
- Morton Clyde 3' 005 6:1 (3:0)
- Celtic Dunfermline Athletic 46' 887 4:0 (4:0)
- Stranraer Falkirk 1' 757 1:2 (0:1)
- Livingston Saint Johnstone 5' 788 1:3 (0:2)
1/16ReplayFansETScore- 1999-02-15Ross County Clydebank 1' 3910:12:2 (1:0)
- 1999-02-09Dundee United Queen's Park 4' 973 1:0 (1:0)
- 1999-02-02Hamilton Academical Saint Mirren 3' 050 1:0 (0:0)
- Albion Rovers Brechin City 457 3:1 (1:1)
- Stirling Albion FCHibernian 3' 643 2:1 (1:1)
Fans Score- 1999-02-03Clydebank Ross County 420 1:1 (0:0)
- 1999-02-02Queen's Park Dundee United 1' 953 0:0 (0:0)
- 1999-01-24Motherwell Heart of Midlothian 9' 372 3:1 (1:0)
- 1999-01-23Saint Johnstone Forfar Ath 3' 717 1:0 (0:0)
- Brechin City Albion Rovers 463 1:1 (0:0)
- Aberdeen Livingston 10' 311 0:1 (0:0)
- Ayr United Kilmarnock 10' 153 3:0 (0:0)
- Falkirk Huntly 3' 018 3:0 (0:0)
- Stranraer East Stirlingshire FC579 1:0 (1:0)
- Saint Mirren Hamilton Academical 2' 361 1:1 (1:0)
- Rangers Stenhousemuir 37' 759 2:0 (2:0)
- Hibernian Stirling Albion FC9' 306 1:1 (0:1)
- Celtic Airdrieonians FC43' 609 3:1 (1:1)
- Morton Dundee FC2' 823 2:1 (2:1)
- Raith Rovers Clyde 2' 581 0:4 (0:2)
- Partick Thistle Dunfermline Athletic 4' 650 1:2 (1:2)
Round 2ReplayFans Score- 1999-01-23Clachnacuddin FCQueen's Park 1' 129 2:3 (0:1)
- 1999-01-18Stirling Albion FCMontrose 625 2:1 (1:0)
- 1999-01-09Stenhousemuir Whitehill Welfare 1' 066 2:0 (0:0)
- Brechin City Keith 688 3:1 (1:0)
- East Fife Forfar Ath 860 0:1 (0:1)
- 1999-01-06Clyde The Spartans FC939 5:0 (2:0)
Fans Score- 1999-01-18Queen's Park Clachnacuddin FC441 1:1 (0:0)
- 1999-01-09Queen of the South Ross County 1' 194 1:3 (0:3)
- 1999-01-02Montrose Stirling Albion FC633 0:0 (0:0)
- Keith Brechin City 539 0:0 (0:0)
- Whitehill Welfare Stenhousemuir 901 1:1 (1:0)
- Huntly Peterhead 1' 137 3:0 (3:0)
- Dalbeattie Star East Stirlingshire FC1' 268 1:2 (1:1)
- The Spartans FCClyde 737 1:1 (1:1)
- Inverness Caled. Th. Livingston 3' 367 1:2 (1:1)
- Partick Thistle Cowenbeath 3' 019 5:2 (2:1)
- Civil Service StrollersAlbion Rovers 322 0:3 (0:2)
- Forfar Ath East Fife 657 2:2 (0:2)
Round 1ReplayFans Score- 1998-12-12Alloa Athletic Stenhousemuir 643 0:2 (0:0)
- 1998-12-08Livingston Dumbarton 449 3:0 (1:0)
Fans Score- 1998-12-05Dumbarton Livingston 530 1:1 (0:0)
- Queen's Park Berwick Rangers 559 2:0 (0:0)
- Stenhousemuir Alloa Athletic 566 1:1 (1:1)
- Arbroath Partick Thistle 1' 333 1:2 (1:2)
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