Originally due to take place in December 2020, the effect of the COVID-19 pandemic on scheduling meant that the match was pushed back to February 2021.
Saints were unseeded for the second round draw and were drawn to face Motherwell at Fir Park on 28 November. Motherwell scored first through Tony Watt, but late goals from Callum Hendry and David Wotherspoon turned the tie around and sent Saints into the quarter-finals.[6]
Saints were again drawn away for the quarter-final, against Championship club Dunfermline Athletic.[7] After a goalless draw in normal time, Shaun Rooney scored the opening goal in the first period of extra time.[7] Dunfermline equalised to force a penalty shootout, which Saints won 4–3.[7]
Livingston were seeded for the second round draw and were drawn to face Championship club Ayr United at home on 28 November.[12] Despite their progress in the League Cup, Livingston had been struggling in the Premiership and manager Gary Holt left the club before the second round tie was played.[12]David Martindale took charge of the team for the first time in the match with Ayr, which Livingston won easily after scoring three early goals through an own goal and two efforts by Jack Fitzwater.[12]
Martindale was still in interim charge for the quarter-final, in which Livi were again drawn at home.[13] They were paired with Ross County, who had knocked out cup holders Celtic in the previous round.[13] Two early goals gave Livi a 2–0 victory.[13]
St Mirren provided the opposition in the semi-final, played at Hampden Park on 24 January. Martindale had been appointed manager on a permanent basis after the quarter-final, and his unbeaten start as a manager continued as an early Scott Robinson goal was enough to give Livingston a 1–0 win.[14] Two days after the semi-final, a Scottish Football Association hearing approved Martindale as a "fit and proper person" to hold a management position.[15] He had previously been imprisoned for involvement with organised crime.[15]
Match
Summary
In the 32nd minute Craig Conway hit an out swinging corner from the right which Shaun Rooney headed down to the right corner from seven yards out, Livingston goalkeeper Robby McCrorie got a hand to the ball to push it against the post and into the net.[16]
