The 1998–99 season was the most successful season in the history of Manchester United Football Club. After finishing the previous season without winning any titles, United won a treble of trophies (the Premier League, FA Cup and UEFA Champions League), the first side in English football to achieve such a feat. During the campaign United lost only five times, including a one-off Charity Shield fixture, in the League Cup against eventual winners Tottenham Hotspur and their only home defeat, a league match against Middlesbrough in December 1998. A run of 33 games unbeaten in all competitions began on 26 December at home to Nottingham Forest.

Veteran players Brian McClair and Gary Pallister, along with a host of younger and less experienced players such as goalkeeper Kevin Pilkington and striker Graeme Tomlinson, had left the club before the season began. The big news of the pre-season was the arrival of Dutch defender Jaap Stam for a club record fee of £10.75 million. Other additions included striker Dwight Yorke and Swedish winger Jesper Blomqvist. Goalkeeper Peter Schmeichel announced his intention to leave the club after eight years at Old Trafford, joining Sporting Clube de Portugal at the end of the season.

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