St. Mirren faced Third Division East Stirlingshire at Ochilview Park in their first match, a comfortable 6–3 victory was secured with five goals from Billy Mehmet and one from Stephen O'Donnell. Mehmet scored one from close range, one from a chip and a third from a header to complete his hat-trick in 17 minutes. The half time score was 3-4 with Memhet scoring all of St. Mirren's goals and Stephen McGuire and an Andy Rodgers brace netting for East Stirlingshire. Memhet and O'Donnell completed the scoring in the second half. St. Mirren then travelled to Somerset Park to play Ayr United, Michael Higdon scored the opener after 25 minutes with a header from a David Barron cross. Dean Keenan was sent off for United in 89 minutes and Billy Memhet scored 66 seconds later to emsure the win. The further trip to Ayrshire awaited St. Mirren in the third round at Rugby Park, the match ended 1-2 to the away team with goals from Stephen McGinn and a 93 minute Andy Dorman strike. The quarter-final opponents were Motherwell at St. Mirren Park. The match ended 3-0 with goals from Michael Higdon, Jack Ross and a Stephen Craigan own goal. Memhet added his eighth goal of the League Cup campaign with the only goal in a 1-0 semi-final win over Hearts at Fir Park.
St. Mirren were without defender Chris Innes due to a torn abductor muscle. Also missing were Rory Loy, who was ineligible under the terms of his loan deal from Rangers, and Tom Brighton. Brighton was ruled out for the rest of the 2009–10 season due to a knee injury.
Rangers defender Madjid Bougherra missed his second successive League Cup final through a hamstring injury. Also missing was Kirk Broadfoot due to a hamstring strain. On 20 March Rangers manager Walter Smith stated that Neil Alexander, usually Rangers' reserve goalkeeper, was to continue in goal for the final, having played in the previous rounds. Midfielder Steven Davis was a late fitness concern with a sickness bug.