1988–89 Manchester United F.C. season

Manchester United talisman Mark Hughes returned to Old Trafford in 1988 after spells in Europe with Barcelona and Bayern Munich for a club record fee of £1.8 million. But Ferguson's other high-profile target, Paul Gascoigne, turned down an opportunity to move to Manchester United despite a verbal agreement between Ferguson and the player and a Maltese holiday paid for by the United manager.[2] Ferguson signed Jim Leighton from former club Aberdeen for £750,000 in order to fill the goalkeeping void left by the retiring Gary Bailey, the underperforming Chris Turner and the injury-prone Gary Walsh.[3]

Manchester United's inconsistency was highlighted early on, recording three consecutive wins; following the 2–0 victory over West Ham United towards the end of September, before failing to record another one until early December, ten games later. Manchester United also recorded six wins from seven games between Boxing Day 1988 and 11 February 1989 before their league season faltered, recording just three more victories in the season.

With the club failing to achieve in the league, many fans began to realise that the cups would be the only realistic opportunity for silverware. They needed three games to defeat Queens Park Rangers in the FA Cup Third Round, before hitting four past Oxford United in the next round. United's three biggest attendances for the season came in the FA Cup, highlighting its importance to the fans, though the campaign eventually ended in defeat at the hands of Brian Clough's Nottingham Forest side in the quarter finals.

Manchester United were also unsuccessful in the season's League Cup; after confidently defeating Rotherham United over two legs, they lost 2–1 to Wimbledon at Plough Lane and were knocked out of the competition.

Before the season began, Paul Gascoigne snubbed Manchester United in favour of a national record move from Newcastle United to Tottenham Hotspur for £2 million, and there was also talk of a similar fee being paid for PSV Eindhoven sweeper Ronald Koeman, who helped the Netherlands win UEFA Euro 1988.

Norman Whiteside and Paul McGrath had been transfer listed at the end of the previous season but the lack of interest in them disappointed Alex Ferguson, who had re-signed striker Mark Hughes from FC Barcelona and brought in goalkeeper Jim Leighton from Aberdeen as successor to Sheffield Wednesday bound Chris Turner. Gordon Strachan agreed terms with Lens of France for a £100,000 transfer, but the deal fell through. Paul McGrath then came off the transfer list at his own request.

On 24 September 1988, Ferguson gave debuts to 17-year-old winger Lee Sharpe and 19-year-old striker Mark Robins in the 2–0 home win over West Ham United in the First Division. This saw United occupy fifth place in the league, level on points with Southampton, a single point behind defending champions Liverpool and newly promoted Millwall, and three points behind surprise leaders Norwich City. However, a 10-match winless league run (8 draws and 2 defeats) followed , dragging them to 11th place in the table by 27 November. The winless streak ended on 3 December with an impressive 3–0 home win over Charlton Athletic.

While United were on their winless streak, they sold out of favour striker Peter Davenport to Middlesbrough for £700,000. They also failed in their Football League Cup quest when they lost 2–1 to Wimbledon at Plough Lane. Brian McClair scored their only goal of the game, while both of Wimbledon's goals were scored by former United striker Terry Gibson.

Alex Ferguson continued to build for the future in November by making a £20,000 move for 21-year-old midfielder Paul Dalton from non-league Brandon United. He also signed 22-year-old winger Giuliano Maiorana from non-league Histon for £30,000.

Five days before Christmas, Jean Busby, wife of legendary former manager and current club president Sir Matt, died after a long illness at the age of 80.

A thrilling clash with Liverpool at Old Trafford on New Year's Day was dominated by 19-year-old midfielder Russell Beardsmore, who scored his first goal for the club and lifted them to sixth in the league, while Liverpool were fifth, and Arsenal and Norwich City were level at the top of the league.

Soon after this successful result, Manchester United were reported to be among the clubs interested in signing Nottingham Forest and England midfielder Neil Webb, who was told by manager Brian Clough that he could leave the City Ground for around £1.5 million after stating that he did not want to sign a new contract.

By 11 February, United were third in the league thanks to a 2–0 win over Sheffield Wednesday that completed a four-match winning run in the First Division, though they were still 11 points behind leaders Arsenal (who had a game in hand) and 8 points behind second placed Norwich City.

Manchester United reached the FA Cup quarter-finals (for the first time since they won the competition four years ago) with a 1–0 home win over AFC Bournemouth in the fifth round replay. , but their last chance of silverware ended when they lost 1–0 at home to Nottingham Forest in the FA Cup quarter-final.

Their form in the final weeks of the league campaign was dismal, as they finished 11th at the end of a season which had begun with such high hopes. Alex Ferguson remained determined to turn his side into title contenders, and just after the season ended he joined the race to sign England winger Trevor Steven, who had been put on the transfer list by Everton. , but was beaten to his signature by Rangers.

A £600,000 offer for Fiorentina and Sweden defender Glenn Hysén was accepted, but he opted to join Liverpool instead.

Several other high-profile names were also mentioned in the media as Ferguson attempted to strengthen his squad. These included West Ham United midfielder Paul Ince, Southampton winger Danny Wallace, Nottingham Forest midfielder Neil Webb and Norwich City midfielder Mike Phelan.