The 1998–99 season was Manchester United Football Club's seventh season in the FA Premier League and their 24th consecutive season in the top division of English football. After finishing the previous season without winning any trophies, United won the Treble of the Premier League, FA Cup, and UEFA Champions League in 1998–99, the first side in English football to do so. During the campaign, United lost only five times: in the Charity Shield against Arsenal; in the fifth round of the League Cup against eventual winners Tottenham Hotspur; and three times in the league, including their only home loss all season, against Middlesbrough in December 1998. A run of 33 games unbeaten in all competitions began on 26 December at home to Nottingham Forest, whom they beat 8–1 away from home in February 1999. The season was characterised by comebacks, including the FA Cup fourth round against Liverpool, the semi-finals of the Champions League against Juventus, and the Champions League final, when Teddy Sheringham and Ole Gunnar Solskjær scored in injury time to overturn Bayern Munich's early lead.

Veteran players Gary Pallister and Brian McClair had left the club before the season began, but their replacements, Dutch defender Jaap Stam from PSV Eindhoven and Trinidadian striker Dwight Yorke from Aston Villa, were both signed for club record fees. In November 1998, goalkeeper Peter Schmeichel announced his intention to leave the club after eight years at Old Trafford, joining Sporting CP at the end of the season. The club was subjected to a takeover bid of more than £600 million from British Sky Broadcasting early in the season, but it was blocked by the Monopolies and Mergers Commission in March 1999.

Fans and writers regard the Treble as manager Alex Ferguson's greatest achievement. In recognition of his success, Ferguson was awarded a knighthood and handed the Freedom of the City of Glasgow in November 1999. David Beckham was named UEFA Club Footballer of the Year for the 1998–99 season, and was runner-up to Rivaldo for 1999's Ballon d'Or and FIFA World Player of the Year awards. the Treble has only been matched once by an English club: by local rivals Manchester City in the 2022–23 season.

Background

Manchester United started the previous season by winning the Charity Shield. However, despite having a 12-point lead above second-placed Arsenal by the start of March, while having played three more matches, Arsenal's eight successive victories, paired with United's 1–0 loss against Arsenal at Old Trafford, meant that United finished second to them in the Premier League by a margin of one point. United exited both the FA Cup in the Fifth Round to Barnsley 3–2 in a replay, and the Champions League to Monaco in the quarter-finals on away goals. Ipswich Town, who were in the second-tier First Division at the time, defeated them 1–0 in the League Cup Third Round.

Ahead of the 1998–99 season, Martin Edwards, the chief executive of the club, questioned manager Alex Ferguson's commitment to the club, who had almost left the club after chairman Roland Smith sent him a letter. Edwards told the Daily Mail:

Pre-season and friendlies Manchester United played four pre-season games ahead of the 1998–99 campaign. After losing 4–3 away to Birmingham City, they toured Scandinavia for three matches, starting with a 2–2 draw against Vålerenga, before comprehensive wins over Brøndby (6–0) and Brann (4–0). After the season began, they played a friendly against a European XI selected by former striker Eric Cantona as a 40-year memorial to the Munich air disaster; Cantona played for both teams during the match, which Manchester United won 8–4. A testimonial for Teddy Scott was scheduled against Aberdeen at Pittodrie in January; United lost 7–6 on penalties after a 1–1 draw in 90 minutes.

DateOpponentsH / AResultF–AScorersAttendance25 July 1998Birmingham CityA3–4Mulryne (3) 21', 38', 56' (pen.)20,70827 July 1998VålerengaA2–2Scholes 12', Solskjær 14'19,70031 July 1998BrøndbyA6–0Sheringham (2) 33', 71', Scholes 44', Cole (2) 66', 84', Cruyff 90'27,0224 August 1998BrannA4–0Irwin (3) 43', 44' (pen.), 55' (pen.), Cole 82'16,10018 August 1998European XIH8–4P. Neville, Butt, Scholes, Giggs, Cantona, Cruyff, Notman (2)55,12118 January 1999AberdeenA1–1(6–7p)Johnsen 51'21,500 Colours: Green = Manchester United win; Yellow = draw; Red = opponents win.

FA Charity Shield

The Charity Shield is played between the previous year's Premier League winner and the FA Cup winner, or the league runners-up if a club won both the league and the FA Cup. Manchester United, as league runners-up, faced the previous season's Double winners Arsenal on 9 August 1998 at Wembley Stadium in front of a crowd of 67,342. Goals from Marc Overmars, Christopher Wreh, and Nicolas Anelka left United losing the game 3–0., Roy Keane made his comeback after almost a year out injured and Jaap Stam made his debut for United.

DateOpponentsH / AResultF–AScorersAttendance9 August 1998ArsenalN0–367,342

FA Premier League

The Premier League is the top division of English league football. 20 clubs play against each other twice, with one match played in a club's stadium and the other in the opponent's stadium. Three points are awarded for a win, one point for a draw, and none for a loss. At the end of the season, the top two teams qualified for next year's UEFA Champions League, the third-placed team qualified for the qualifying rounds of the Champions League, the fourth-placed team qualified for the UEFA Cup, and the bottom three teams were relegated to the Football League First Division.

August–October In the first match of the season, Manchester United faced Leicester City at Old Trafford and went a goal down within seven minutes, when Emile Heskey turned in Muzzy Izzet's cross via the crossbar. Tony Cottee – the scorer in the previous season's corresponding fixture – added a second with 15 minutes remaining. A long-range shot from David Beckham deflected in off Teddy Sheringham three minutes later, before Beckham himself scored with a direct free kick to salvage a point for the home side. The team's first away game followed at West Ham United, but despite the debut of striker Dwight Yorke, United were held to a goalless draw. Beckham, who had become a national hate figure after his dismissal at the World Cup, was poorly received by West Ham supporters, with his every touch of the ball jeered. Bottles and stones were directed at the team bus prior to kick-off. After the game, Ferguson, his players, and the Manchester United staff refused to be interviewed by the press or television.

Manchester United recorded their first win of the season on 9 September, beating newly promoted Charlton Athletic 4–1. Yorke and Ole Gunnar Solskjær each scored a brace to overturn the visitors' early lead. Old Trafford was covered in graffiti against the proposed takeover of the club by BSkyB. Chants were directed at chairman Martin Edwards, who had given his support to the merger. The following week, ahead of their midweek UEFA Champions League group stage visit against Barcelona, United earned a 2–0 victory against Coventry City, thanks to goals from Yorke and Ronny Johnsen. However, a 3–0 defeat to defending champions Arsenal left the team in 10th place after five matches, with Arsenal winning against United in four consecutive matches; goals from Tony Adams, Nicolas Anelka, and Freddie Ljungberg condemned Manchester United to their second 3–0 defeat by Arsenal in the season. Midfielder Nicky Butt, who had been sent off in the Champions League match earlier in the week, was handed a second red card in the space of four days for a foul on Patrick Vieira. After the match, Alex Ferguson admitted that his team was inferior to Arsenal, and later called their performance "depressing".: "Our performance was so disappointing, even depressing[.]" United ended the month with a win, beating rivals Liverpool 2–0 to move into fifth spot, with Denis Irwin scoring a penalty and Paul Scholes scoring a cross from Andy Cole.

A trip to face Southampton at The Dell on 3 October was taken with caution, given United's return from Munich in the Champions League and poor record on the ground: United had lost to Southampton on each of their last three visits, including a 6–3 defeat in 1996. Cole was paired with Yorke for only the second time in the season, a tactic that paid off as both got on the scoresheet. Substitute Jordi Cruyff added a third in the 75th minute to move United into second place in the table, four points behind leaders Aston Villa. An international break followed the game, pausing club football for two weeks. Upon their return, Raimond van der Gouw, who deputised for injured goalkeeper and captain Peter Schmeichel at Southampton, featured again at home to Wimbledon, a match that Manchester United won 5–1, the biggest win of the season at Old Trafford. Ryan Giggs, Beckham, Yorke, and Cole all scored, with Cole scoring twice; Ferguson, in particular, hailed the contribution of 19-year-old defender Wes Brown. United earned a point away at Derby County on 24 October, with Cruyff scoring a late equaliser for United following Darryl Powell's goal, and beat Everton 4–1 at Goodison Park on 31 October to cut the gap at the top to just a point.

November–December

Manchester United failed to score in a goalless draw against Newcastle United, but made amends with a 3–2 victory over the bottom team, Blackburn Rovers. Defensive frailties, most notably from Schmeichel, who had announced his intention to leave Manchester United at the end of the season, were on show away to Sheffield Wednesday as the team missed the chance to go top of the table, losing 3–1. A brace from winger Niclas Alexandersson and a debut goal scored by Wim Jonk consigned Ferguson to his second defeat in the league and extended a barren run at Hillsborough: United had won only a single game in their last eight league visits. On 29 November, Manchester United hosted Leeds United; Leeds opened the scoring with just under half an hour played, but a goal either side of half-time gave United the lead. Leeds equalised in the 52nd minute, Butt scored after receiving the ball from Phil Neville and spinning around, securing three points for United.

Three straight draws followed in December, the first away to league leaders Aston Villa. United were fortunate to pick up a point given their opponents' dominance in the second half. At the match against Tottenham Hotspur, United surrendered a 2–0 lead: Solskjær put United two goals ahead, but in the 39th minute, Gary Neville received a red card for a second bookable offence, tugging on David Ginola's shirt. Spurs captain Sol Campbell brought his team back into the match with 20 minutes remaining and powered a header into the top left-hand corner just before full-time. Ferguson refused to comment after the match. Despite losing the lead, the result put United top of the league on goal difference ahead of Aston Villa, before they faced Arsenal the following day.