Scottish League Challenge Cup 2008-09
Sponsored by Alba
First Round
North & East Region
- Alloa Athletic 2-1 Dundee
- Arbroath 1-2 Forfar Athletic
- Brechin City 0-1 East Fife
- Dunfermline Athletic 3-0 Stirling Albion
- Elgin City 0-2 Cowdenbeath
- Peterhead 6-0 Montrose
- Ross County 2-1 St Johnstone
- Raith Rovers - Bye
South & West Region
- Airdrie United 3-2 Dumbarton
- Berwick Rangers 1-5 Queen of the South
- Clyde 2-0 Annan Athletic
- Livingston 4-0 Stranraer
- Partick Thistle 2-1 Queen's Park
- Stenhousemuir 0-1 Albion Rovers
- East Stirlingshire 2-1 Ayr United
- Morton - Bye
Second Round
- Alloa Athletic 0-2 Clyde
- Cowdenbeath 3-2 Albion Rovers
- Livingston 1-0 Forfar Athletic
- Partick Thistle 4-2 Peterhead
- Raith Rovers 1-2 Ross County
- East Fife 0-2 Airdrie United
- East Stirlingshire 0-3 Morton
- Dunfermline Athletic 0-2 Queen of the South
Quarter Finals
- Clyde 0-1 Ross County
- Cowdenbeath 1-2 Airdrie United
- Livingston 0-2 Partick Thistle
- Queen of the South 0-2 Morton
Semi-Finals
- Partick Thistle 0-1 Airdrie United
Final (@ St Johnstone, 16/11/08)
- Airdrie United 2-2 Ross County (Airdrie United won 3-2 on penalties)
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