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FinalFans Score- 2009-11-22Dundee FCInverness Caled. Th. 8' 031 3:2 (0:2)
1/2Fans Score- 2009-10-04Dundee FCAnnan Athletic 2' 321 3:0 (1:0)
- Inverness Caled. Th. Ross County 2' 275 1:0 (1:0)
1/4FansPenETScore- 2009-09-06Partick Thistle Inverness Caled. Th. 1' 7463:40:01:1 (0:1)
- Ross County Queen of the South 964 2:0 (1:0)
- Stirling Albion FCDundee FC1' 277 1:2 (0:2)
- Annan Athletic Elgin City 534 4:2 (0:2)
1/8Fans Score- 2009-08-18Annan Athletic East Stirlingshire FC357 1:0 (0:0)
- Elgin City Albion Rovers 245 3:0 (0:0)
- Ross County Morton 588 2:1 (0:0)
- Stirling Albion FCStenhousemuir 275 3:1 (1:0)
- Inverness Caled. Th. Stranraer 643 3:0 (3:0)
- Cowenbeath Dundee FC457 0:3 (0:1)
- Dunfermline Athletic Queen of the South 941 1:2 (0:1)
- Forfar Ath Partick Thistle 532 1:6 (0:1)
Round 1Fans Score- 2009-07-26Dumbarton Morton 1' 122 0:1 (0:1)
- 2009-07-25Inverness Caled. Th. Montrose 1' 0725:40:01:1 (1:0)
- Ross County Alloa Athletic 748 2:11:1 (0:1)
- Stenhousemuir Clyde 603 2:0 (0:0)
- Ayr United Albion Rovers 979 0:2 (0:0)
- Dunfermline Athletic Arbroath 1' 708 2:1 (0:0)
- Airdrieonians FCPartick Thistle 1' 325 0:1 (0:0)
- Elgin City Brechin City 381 3:1 (1:0)
- Annan Athletic Queen's Park 411 2:0 (1:0)
- Peterhead Cowenbeath 361 1:2 (1:0)
- Queen of the South Livingston 1' 558 1:0 (1:0)
- Stirling Albion FCRaith Rovers 713 2:1 (1:0)
- East Fife Forfar Ath 446 0:2 (0:1)
- Stranraer Berwick Rangers 245 4:2 (2:1)
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