1999–2000 FA Cup
| Country |
 England Wales
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|---|---|---|---|
| Champions | Chelsea (3rd title) | ||
| Runners-up | Aston Villa | ||
| Top goal scorer(s) |
Gustavo Poyet (6 goals) |
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|
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The 1999–2000 FA Cup was the 119th staging of the world's oldest cup competition, the Football Association Cup or FA Cup. Both the semi-finals and final of the competition were played at Wembley Stadium for the last time before reconstruction work began. The competition culminated with the FA Cup Final between Chelsea and Aston Villa. The game was won by a goal from Chelsea's Roberto Di Matteo, giving them a 1-0 victory.
The previous season's winners, Manchester United, withdrew from the 1999–2000 competition due to their participation in the 2000 FIFA Club World Championship in South America, to take place in early 2000, thus becoming the first FA Cup winners not to defend their title. Despite this being at the request of the Football Association (FA), they received criticism from journalists and television pundits. To keep the competition running smoothly, the FA chose to draw one team from among those lower-division teams defeated in the second round to progress as "lucky losers" to the third.Darlington were the team drawn.
The main competition started in November 1999 for clubs from the Football League and Premiership. For details on the preliminary and qualifying rounds of the FA Cup see FA Cup Archives.
Manchester United, who were the winners the previous season, did not enter.
This round is the first in which teams from the First Division and Second Division compete with non-league teams.
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