The 2000 FA Charity Shield (also known as The One 2 One FA Charity Shield for sponsorship reasons) was the 78th FA Charity Shield, an annual football match organised by the Football Association, and contested by the winners of the previous season's Premier League and FA Cup competitions. It was the final club match played at the original Wembley Stadium in London and took place on 13 August 2000 between Chelsea, the winners of the 1999–2000 FA Cup, and Manchester United, who had won the 1999–2000 FA Premier League. Watched by a crowd of 65,148, Chelsea won the match 2–0.

This was Chelsea's 4th appearance in the Shield and Manchester United's 20th. It was the second time they had met in the competition. Chelsea were without Albert Ferrer, who had sustained a chest injury in pre-season, while Graeme Le Saux made his first appearance in 10 months after recovering from an ankle injury. Three of Chelsea's new signings made their debuts for the team, with Jimmy Floyd Hasselbaink, Eiður Guðjohnsen and Mario Stanić named in the squad, while goalkeeper Fabien Barthez was Manchester United's only debutant.

Chelsea took the lead in the 22nd minute when Hasselbaink's shot deflected off Jaap Stam and over Barthez after the Dutch striker was put through on goal by a Gus Poyet header. Manchester United captain Roy Keane was shown a red card midway through the second half for a tackle on Poyet. Minutes later, Chelsea scored a second goal through Mario Melchiot, who shot left-footed low past the legs of Stam and Barthez. No further goals were scored and Chelsea took the Charity Shield for the second time, 45 years after their first in 1955. It was the third year in succession that Manchester United had been defeated in the competition, the first club to suffer the feat.

Founded in 1908 as a successor to the Sheriff of London Charity Shield, the FA Charity Shield began as a contest between the respective champions of the Football League and the Southern League, although in 1913 it was played between an Amateurs XI and a Professionals XI. In 1921, it was played by the First Division champions and FA Cup winners for the first time. The match in 2000 was the 27th and last Charity Shield to be played at the original Wembley Stadium before it was demolished for renovation. The host broadcaster was Sky Sports, who provided main commentary from Martin Tyler and Andy Gray, as well as an alternative feed dubbed "FanZone" via the interactive Sky Digital platform, with a fan from each team providing commentary.

Chelsea qualified by way of winning the 1999–2000 FA Cup, their second FA Cup title in the previous four years. They defeated Aston Villa 1–0 in the final. Manchester United had qualified for the Charity Shield by winning the 1999–2000 FA Premier League, their sixth league championship in eight years. They had scored a league-high 97 goals and won the title by a then-record margin of 18 points over second-placed Arsenal. Chelsea were appearing in the Charity Shield for a fourth time; they had won in their first appearance in 1955, and lost in 1970 and 1997. This was Manchester United's 20th appearance in the competition; they had won ten (1908, 1911, 1952, 1956, 1957, 1983, 1993, 1994, 1996, 1997), shared four (1965, 1967, 1977, 1990) and lost five (1948, 1963, 1985, 1998 and 1999). By their fifth consecutive appearance, United surpassed the record of four they shared with Arsenal and Everton, who respectively achieved that feat between 1933 and 1936, and 1984 and 1987. The 2000 match was the second meeting between these two clubs in the Shield; Manchester United won the previous encounter in 1997 4–2 in a penalty shoot-out after a 1–1 draw in normal time.

Manchester United manager Alex Ferguson said before the match that he was pleased that his side was one of the teams to play in the final Charity Shield match to be contested at the old Wembley Stadium and was hoping the win could give the team a good start stating: "The Charity Shield is not the most important fixture, but nonetheless it is preparation – and in preparation you want to do well. We want to see some progress from the games that we've had so far and the training." Gianluca Vialli, the Chelsea manager, used his press conference to emphasise that new signings Jimmy Floyd Hasselbaink and Eiður Guðjohnsen would score additional goals for the club and spoke of the Charity Shield's significance, saying: "It is a very important match for us as we can win a trophy and put it in our cabinet. That would be the best way to start a new season – beating the champions at Wembley and winning a trophy."

Phil Neville, a defender for Manchester United, was told by Ferguson to expect verbal abuse from the spectators during the match because he was blamed for bringing about England's exit from UEFA Euro 2000 after a 3–2 defeat to Romania two months prior. He had already received abuse in a pre-season friendly match against Shrewsbury Town of which Ferguson said: "When you play away from home, you're hardly going to get bouquets of flowers thrown at you. That's not going to change, but I think Phil is capable of handling it. I expect his team-mates to help him through it. That's what teams are about. That's what the word 'team' means."

Paul Johnson of Racing Post opined that Chelsea would be the team more likely to win the Charity Shield even though the two clubs had each won 8 of their last 16 encounters. The football correspondent of the Sydney-based Daily Telegraph wrote that other clubs will focus on Manchester United's weaknesses rather than the final score of the match. Mike Riley was selected as the referee for the match; Uriah Rennie was originally slated to take charge of the match before it was discovered that he had been demoted from the list of Premier League referees, and he ultimately served as fourth official. Neither club sold out their allocation of tickets, with Chelsea selling 27,000 out of 30,000 reserved.