During the 1999–2000 English football season, Wimbledon competed in the Premier League (known as the FA Carling Premiership for sponsorship reasons).
The season began with a new manager, Norway's Egil Olsen, after the close season resignation of long-serving Joe Kinnear, but Olsen was ousted with two weeks of the season remaining and replaced by coach Terry Burton, who was unable to save Wimbledon from relegation after 14 successive seasons of top division football.
The close-season resignation of former Joe Kinnear because of health problems (he would suffer from them again as manager of Newcastle United) after seven years as manager led to the appointment of former Norwegian national coachEgil Olsen as Wimbledon's new manager, giving Dons fans hope of beating the drop once again. The mid-season collapse of star striker John Hartson's move to Tottenham Hotspur was further good news to the cause, but a run of eight straight defeats during the final weeks of the season dragged Wimbledon into the depth of the relegation mire. Olsen was sacked after a 3–0 defeat away to Bradford City, to be replaced by former coach and assistant manager Terry Burton for the final two games of the season. A 2–2 draw at home to Aston Villa gave them hope going into their last game, away to Southampton. They were one place above the relegation zone on goal difference, but a 2–0 defeat at the Dell – combined with Bradford's 1–0 win over Liverpool – condemned Wimbledon to relegation and ended their 14-year stay in the top flight. The transition coincided with the end of one of the most remarkable rags-to-riches stories in football,[according to whom?] which had started with Wimbledon's election to the Football League in 1977 and seen them reach the top flight nine years later, before peaking as 1988 FA Cup Final winners. Their relegation was confirmed 12 years to the day that Wimbledon achieved their famous victory over Liverpool at Wembley.
^Sullivan was born in Sutton, England, but qualified to represent Scotland internationally and made his debut for Scotland in 1997.
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^Cort was born in Southwark, England, but qualified to represent Guyana and would make his international debut for Guyana in 2011.
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^Euell was born in Lambeth, England, but also qualified to represent Jamaica internationally and would make his international debut for Jamaica in 2004.
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^Ekoku was born in Manchester, England, but qualified to represent Nigeria internationally and made his international debut for Nigeria in 1994.