2008–09 Scottish League Cup
The 2008–09 Scottish League Cup was the 63rd season of the Scotland's second most prestigious football knockout competition, also known for sponsorship reasons as the Co-operative Insurance Cup. Celtic won the cup beating Rangers 2–0 after extra time thanks to a goal from Darren O'Dea and an Aiden McGeady penalty.
First round
The First round draw was conducted at Hampden Park on 2008-07-22.Source:
Second round
The second round draw was conducted at The Signet Library, Edinburgh on 2008-08-11.Source:
Third round
The Third round draw was conducted at Hampden Park, Glasgow on 2008-09-01.Source:
Quarter-finals
The quarter-final draw was conducted at Hampden Park, Glasgow on 25 September 2008.----
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Semi-finals
The semi-final draw was conducted at the Scottish Parliament, Edinburgh on 12 November 2008 by First Minister Alex Salmond, a representative of sponsors Co-operative Insurance and the Presiding Officer of the Parliament, Alex Fergusson.----
Awards
A team, player and young player were chosen by the Scottish sports press as the top performers in each round.| Round | Team | Player | Young player | Ref |
| R1 | Greenock Morton | |||
| R2 | Greenock Morton | Stephen Robertson | Leigh Griffiths | |
| R3 | Dunfermline Athletic | Conor Sammon | David Goodwillie | |
| QF | Scott Robertson | Scott Arfield |