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,[1] 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.[2] 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.[3]Darlington were the team drawn.[4]
The main competition started in November 1999 for clubs from the Football League and Premiership.
Calendar
Round
Date
Matches
Clubs
New entries this round
Prize money
Preliminary round
21 August 1999
166
558 → 392
161: 227th–387th
£1,000
First round qualifying
4 September 1999
116
392 → 276
66: 161st–226th
£2,250
Second round qualifying
18 September 1999
80
276 → 196
44: 117th–160th
£3,750
Third round qualifying
2 October 1999
40
196 → 156
none
£5,000
Fourth round qualifying
16 October 1999
32
156 → 124
24: 93rd–116th
£10,000
First round proper
30 October 1999
40
124 → 84
48: 45th–92nd
£16,000
Second round proper
19 November 1999
20
84 → 64
none
£24,000
Third round proper
11 December 1999
32
64 → 32
43: 2nd–44th‡
£40,000
Fourth round proper
8 January 2000
16
32 → 16
none
£60,000
Fifth round proper
29 January 2000
8
16 → 8
none
£120,000
Sixth round proper
19 February 2000
4
8 → 4
none
£300,000
Semi-finals
2 April 2000
2
4 → 2
none
£900,000
Final
20 May 2000
1
2 → 1
none
£1,000,000
‡ Manchester United, who were the winners the previous season, did not enter.
The shock result of the round came when Division Two Gillingham (who had yet to play in the top two divisions) defeated Premier League side Sheffield Wednesday 3–1.
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).
Aston Villa win 4–1 on penalties. Steve Stone, Lee Hendrie, Gareth Barry and Dion Dublin all scored for Aston Villa. Dean Holdsworth scored for Bolton.
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.
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.[citation needed]