The 1999–2000 FA Cup (known as The FA Cup sponsored by AXA for sponsorship reasons) was the 119th staging of the FA Cup. Both the semifinals and final of the competition were played at Wembley Stadium for the last time before reconstruction work began. The competition culminated with the 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 title holders 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.

Calendar

Manchester United, who were the winners the previous season, did not enter.

First round proper

This round is the first in which teams from the second Division and Third Division compete with non-League teams. ‡ - Oxford City's replay with Wycombe Wanderers was abandoned after extra time due to a fire within the stadium. The score was 1–1.

Second round proper

= Darlington advanced as lucky losers

Third round proper

This round marked the first time First Division and Premier League (top-flight) teams played.

Fourth round proper

Fifth round proper

Sixth round proper

Semi-finals

Aston Villa booked their first FA Cup final appearance since 1957 by beating Bolton Wanderers on penalties after a goalless draw, while Chelsea reached their second final in four years with a narrow 2–1 win over Newcastle United (who had been finalists in the previous two seasons).

Final

The 2000 FA Cup final was contested between Chelsea and Aston Villa at Wembley Stadium, with Chelsea coming out 1-0 winners. Roberto Di Matteo scored the winning goal 17 minutes from the end, three years after he had opened the scoring within the first minute of Chelsea's last FA Cup final win. This was Villa's first FA Cup final for 43 years.

Media coverage

In the United Kingdom, ITV were the free to air broadcasters for the third consecutive season while Sky Sports were the subscription broadcasters for the twelfth consecutive season. The matches shown live on ITV Sport were: The matches shown live on Sky Sports were: