1991 Football League Cup final

Manchester United's second-round tie saw them drawn against Fourth Division Halifax Town; they won the first leg at The Shay 3–1, with goals from Clayton Blackmore, Brian McClair and Neil Webb, before Viv Anderson and Steve Bruce gave them a 2–1 win at Old Trafford and a 5–2 aggregate victory. Anderson, who was by now rarely used in the United first team, went on to be sold to Sheffield Wednesday three months later, his appearance for United in the early stages of the competition making him ineligible for Wednesday's matches and denying him the chance to add to the two League Cup medals he had won with Nottingham Forest and a later medal in the competition won with Arsenal.

They were then drawn against rivals and reigning First Division champions Liverpool in the third round, where Mark Hughes and Lee Sharpe joined Bruce on the score sheet in a 3–1 home win. In the fourth round, a 19-year-old Sharpe scored a hat-trick in addition to goals from Blackmore, Hughes and Danny Wallace to give United a 6–2 away win over Arsenal, who would go on to win the First Division title that season, just over a month after the two teams had been involved in a mass brawl during a 1–0 Arsenal win at Old Trafford that saw both teams deducted points.

In the fifth round, United were held to a 1–1 draw away to Southampton, Hughes scoring their only goal; Hughes was again the only United player on the score sheet in the replay a week later, scoring a hat-trick in a 3–2 win that put them into the semi-finals. Southampton striker Alan Shearer, who within months was reported to be transfer target for Manchester United, scoring all of Southampton's goals during the two cup clashes with United.

Goals from McClair and Sharpe gave United a 2–1 win in the first leg of the semi-final at home to Leeds United, and Sharpe scored again in the second leg – his sixth League Cup goal of the season – as United won 1–0, and 3–1 on aggregate, to put them into their second League Cup final.

Sheffield Wednesday, whose last major honour had been the FA Cup in 1935, were fresh from relegation to the Second Division when they were drawn against Third Division Brentford in the second round, winning 2–1 in each of the two legs to put them into the third round. There they met fellow Second Division side Swindon Town, who held them to a goalless draw at Hillsborough, before succumbing to a 1–0 defeat at the County Ground in the replay a week later. Wednesday required another replay in the fourth round, after they played out another draw at home to Derby County, but beat them 2–1 at the Baseball Ground two weeks later.

The quarter-final saw Wednesday drawn away to Coventry City, where a 1–0 victory for Wednesday ended any hopes that Coventry's new player-manager Terry Butcher might have had of beginning his managerial career with silverware. Their semi-final opponents were Chelsea. The first leg of the semi-final was played at Stamford Bridge, where goals from Peter Shirtliff and David Hirst gave them a 2–0 win, before Nigel Pearson, Danny Wilson and Paul Williams gave them a 3–1 win in the second leg at Hillsborough to put them into the final, 5–1 on aggregate. It was Wednesday's first Wembley cup final in 25 years.