The 1999 Football Association Charity Shield (also known as the One 2 One FA Charity Shield for sponsorship reasons) was the 77th FA Charity Shield, an annual English football match played between the winners of the previous season's Premier League and FA Cup competitions. The teams involved were Manchester United, who had won both the Premier League and FA Cup as part of the Treble the previous season, and Arsenal, who finished runners-up in the league. Watched by a crowd of 70,185 at Wembley Stadium, Arsenal won the match 2–1.
This was Arsenal's 15th Charity Shield appearance and Manchester United's 19th. Leading up to the match, both clubs were embroiled in controversy: United withdrew from English football's primary cup competition, the FA Cup, in order to take part in the 2000 FIFA Club World Championship; Arsenal were entangled in a transfer saga involving their own player, striker Nicolas Anelka, who vowed to never play for the club again. United goalkeeper Mark Bosnich, signed as a replacement for Peter Schmeichel, made the first appearance of his second spell with the club. Sylvinho started his first game for Arsenal, whereas other signing Oleh Luzhny was named on the substitutes' bench. United went ahead seven minutes before the end of the first half, when David Beckham's free-kick hit the underside of the crossbar and narrowly crossed the line before Dwight Yorke made sure. Arsenal were awarded a penalty in the second half which Nwankwo Kanu converted and the striker assisted his teammate Ray Parlour to score the winner.
This result marked Manchester United's first defeat of 1999. It was the second consecutive year that Arsenal beat United to win the Charity Shield. Arsenal manager Arsène Wenger described it as psychological boost to beat his opponents and felt the win showed that his team were ready for the upcoming season. United manager Sir Alex Ferguson, on the other hand, believed the defeat highlighted his players needed more game time.
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 Southern League, although in 1913, it was played between an Amateurs XI and a Professionals XI. In 1921, it was played by the league champions of the top division and FA Cup winners for the first time. Wembley Stadium acted as the host of the Shield from 1974.
Manchester United qualified for the 1999 FA Charity Shield as winners of the 1998–99 FA Premier League. The team overcame close competition from Arsenal to win their fifth league title in seven years. In the 1999 FA Cup Final, Manchester United beat Newcastle United by two goals to nil and completed the domestic double. The team later went on to win the UEFA Champions League after defeating Bayern Munich in the season's final and became the first English team to acclaim a treble of trophies in one season. Given United won both domestic honours, the other Charity Shield place went to league runners-up Arsenal. United appeared in 18 previous Shields, winning 10 outright (1908, 1911, 1952, 1956, 1957, 1983, 1993, 1994, 1996, 1997), sharing four (1965, 1967, 1977, 1990) and losing four (1948, 1963, 1985, 1998). In contrast, Arsenal won eight previous Shields (1930, 1931, 1933, 1934, 1938, 1948, 1953, 1998), shared one with Tottenham Hotspur in 1991 and lost five (1935, 1936, 1979, 1989, 1993).
The most recent meeting between the two clubs was in the FA Cup semi-finals; the tie was decided by a replay as the initial game finished goalless. The match was settled in extra time when Giggs ran the length of the pitch and evaded several Arsenal players to score the winning goal. In the close season, Anelka was involved in a protracted transfer saga and vowed to never play for Arsenal again. He cited the media in England as a reason for wanting to leave the club: "The one thing I can tell you is that I can't stand the English Press, who cause me enormous problems on a personal level," but it was implied that his "gold-digging brothers" wanted Anelka to move abroad to make more money – they served as his agents.
In June 1999, United accepted an offer from the FA to withdraw from the FA Cup in order to participate in the 2000 FIFA Club World Championship, staged in Brazil. It was criticised by the new Sports minister Kate Hoey, who suggested the club were treating its supporters in a "shabby way". Manchester United manager Sir Alex Ferguson however replied that United had been pressurised to make the decision, which aimed to solidify England's 2006 FIFA World Cup bid: "The Government are saying that we should be in the FA Cup, but they are the very people that were saying originally that we have to go to Brazil. They could tell us quite clearly: 'Do not bother about the World Cup bid, leave that to us. It should not be Manchester United's responsibility.'"
Arsenal manager Arsène Wenger revealed before the Charity Shield game that he was not overly concerned with Anelka leaving, rather the injuries that were depleting his squad: "I cannot forget that it was because of a poor start to last season that we lost the championship to Manchester United." He refused to categorise the match as a "friendly" much like it is traditionally viewed as: "There is a trophy and medals at stake. We won it last season and our players want to win it again." Ferguson described the 3–0 defeat in the previous season's Shield as a "humiliation", before discussing how it made the team prepare for the challenges ahead: "I have reminded the players how hard it is to lose when you are playing for United these days – it makes so many other people happy." Indeed, United only lost five matches of the whole of last season, with their last defeat coming at home to Middlesbrough in December 1998.
Both teams were without several first team players because of injury problems. Manchester United midfielder Roy Keane was absent, which meant defender Denis Irwin took responsibility as the team captain. Ryan Giggs was also ruled out of the game, though his injury was unspecified. Forwards Andy Cole and Dwight Yorke started upfront for United, in a 4–4–2 formation where David Beckham and Jordi Cruyff acted as the two wide midfield players. Goalkeeper Mark Bosnich, signed as a replacement for Peter Schmeichel, also started, having rejoined the club after a nine-year spell with Aston Villa.
For Arsenal, defender Tony Adams was ruled out with injury, as was Dennis Bergkamp, Marc Overmars, and goalkeeper David Seaman. Anelka did not partake, given his transfer to Real Madrid was on the verge of being completed. New signings Oleh Luzhny and Sylvinho were both named in the squad, but whereas Sylvinho started the game, Luzhny was selected as a substitute. Arsenal, like United, lined up in a 4–4–2 formation. Up front, Fredrik Ljungberg was paired with the club's only available recognised striker, Nwankwo Kanu.
The severe heat meant Manchester United and Arsenal found it hard to find any rhythm early on. Sylvinho fashioned an early chance for Arsenal, though his shot was deflected over. Although midfield pair Patrick Vieira and Emmanuel Petit did well to contain their opponents in the opening half-hour, Arsenal's lack of pace and incisiveness upfront was evident – Ljungberg missed three chances before half-time. Midway through the first half, Beckham was booked by referee Graham Barber for dissent. Moments later Nicky Butt was involved in a brawl with Martin Keown, after the defender nearly caught Butt's face with his boot. Both players were booked for confronting each other, as was Vieira for getting involved. United performed better the longer the match went on and scored the opening goal. Beckham's 30 yards (27 m) free kick hit the underside of the crossbar and bounced out; Yorke headed the rebounded ball past goalkeeper Alex Manninger. Although replays suggested the goal was Beckham's as his free kick crossed the goal line, it was given to Yorke. Arsenal responded for a short while, but missed "three half-chances".
Defender Jaap Stam, "nursing an Achilles injury all summer", was substituted in the second half for David May. Arsenal began the half the better of the two teams and Vieira believed he earnt his team a penalty in the 49th minute – it was turned down by Barber. The substitution of Sylvinho for Luis Boa Morte in the 64th minute allowed Ljungberg to play in a natural midfield role. Two minutes later, Arsenal were awarded a penalty. Vieira, chasing down the ball was adjudged to have his shirt tugged by Irwin in the 18-yard box. Kanu converted the penalty, sending Bosnich the wrong way. Yorke soon after mistimed his goal effort after being sent clear by Cole. Substitute Ole Gunnar Solskjær then put Cole through, only for Manninger to produce a one-handed save. Arsenal scored what proved to be the match winner in the 78th minute. A goal-kick by Bosnich was headed back into United's half by Vieira; Kanu controlled the ball "deftly" and set up Parlour, whose shot went into the net. Teddy Sheringham was brought on by Ferguson for Butt with nine minutes of normal time remaining, but with a fourth striker on the field, United were unable to score an equaliser. Luzhny later came on for Parlour, the final substitution of the match.
The result marked the first time that Manchester United had lost in the calendar year, ending a 33-match unbeaten run. Wenger believed the result showed that Arsenal were "ready for the season", albeit admitting that the defence had trouble coping with Yorke. He thought it was "...psychologically important to beat United, especially after the great run they have had". Wenger confirmed afterwards that Anelka would sign for Real Madrid: "I hope everything will be finalised in the next couple of days. In any case, he is not coming back here, and although the contract is not signed yet, I hope it will be after his medical and that is the end of it." Kanu, who scored Arsenal's equaliser and set up the match winner, was pleased with his performance and relished the opportunity of establishing himself in the first team, after Anelka's departure.
Ferguson said the defeat showed that Manchester United needed more games to be ready, "particularly, in the second half" and felt travelling "half way across the world" for pre-season did not aid their preparation. In terms of the result, he said it was "about as significant" as it was last year. Bosnich's performance in goal received mixed reviews in the English press; The Sun questioned his positioning and said his kicking was "poor". The player himself assessed: "My kicking has been atrocious and, generally, my distribution from the back has to improve."