1999–2000 FA Cup

Both the semifinals and final of the competition were played at Wembley Stadium for the last time before reconstruction work began.

The game was won by a goal from Chelsea's Roberto Di Matteo, giving them a 1–0 victory.

‡ - Oxford City's replay with Wycombe Wanderers was abandoned after extra time due to a fire within the stadium.

[5] ^† = Darlington advanced as lucky losers This round marked the first time First Division and Premier League (top-flight) teams played.

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).