As Hearts finished in the top five of the SPL, they entered the League Cup in the third round. They made a convincing start, defeating Livingston in third round. A much tougher test awaited the Jambos in the shape of Dundee United in the quarter-finals, although they defeated the 2008/09 semi-finalists on penalty kicks. Hearts came up against Inverness CT in the semi-finals at Easter Road and were again victorious on penalties.
St. Mirren finished 8th in the SPL and entered the League Cup in the second round. They too made a fantastic start, thrashing Ayr United. Hamilton were the Buddies' opponents in the third round and Danny Lennon's men sneaked through after a goal in stoppage time. The quarter-finals saw the Saints take a trip up to Pittodire to face Aberdeen, and after a 2–2 draw after extra time, the men from Paisley won on penalties. A trip to Hampden Park for the semi-finals saw St. Mirren run out 3–2 winners against Celtic and set up a final against Hearts. St. Mirren won the final 3-2 against Hearts. It was their first trophy since the 1987 Scottish Cup victory.