Watford went down in bottom place with a record Premiership low of 24 points. Sheffield Wednesday were next to go down. On the last day of the season, Wimbledon lost 3-0 at Southampton and Bradford City achieved a shock 1-0 home win over Liverpool. This meant that Bradford had survived the drop and Liverpool had surrendered a UEFA Champions League place. It also meant that Wimbledon's 14-year spell in the top flight was over and they were relegated to Division One 12 years to the day that they had beaten Liverpool to achieve a shock FA Cup triumph.
1999–2000 also saw some of Division One's biggest clubs miss out on promotion—the biggest of these were Blackburn Rovers (11th) and Nottingham Forest (14th). Steve Coppell ended his fourth spell as Crystal Palace manager after doing wonders to keep a virtually bankrupt club clear of the Division One relegation zone.
Going down were Walsall, Port Vale and Swindon Town. West Bromwich Albion just missed out on the drop zone thanks to a late turn-around in form during the final weeks of the season which followed the appointment of Gary Megson as manager.
Division Two
David Moyes, 37, showed promise as one of the league's most highly rated young managers after he guided Preston North End to the Division Two championship. Stan Ternent's two-year rebuilding project at Burnley paid off as they finished runners-up in the division. Joining them in Division One were Peter Taylor's Gillingham, who had reached the upper half of the league for the first time in their history.
Chester City were relegated on the last day of the season, ending their 69-year league career while Shrewsbury Town and Carlisle United saved themselves from Conference football.
FA Cup
Chelsea beat Aston Villa 1-0 in the last FA Cup final at Wembley before its redevelopment. The competition was played despite the absence of holders Manchester United due to FIFA Club World Cup commitments. Their absence meant that in the 3rd round of the competition, there was an uneven number of teams, and so Darlington FC were picked out of a hat of "lucky losers" and played against Aston Villa despite having lost in the 2nd round of the competition. Villa beat them 2-1.
In a one-off season, most FA Cup rounds were played a few weeks earlier than their traditional dates. For example, the first round was played in late October (rather than mid-November) and the third round was held on the second Saturday in December (instead of its annual place at the start of the new year). The experiment has not been repeated since.
Manchester United retained their Premiership title after losing just three league games all season and finishing 18 points ahead of runners-up Arsenal. Roy Keane was voted Player of the Year by both the PFA and FWA and Andy Cole finished as the club's top scorer with 19 Premiership goals. United lost their defence of the European Cup after losing to eventual winners Real Madrid in the quarter finals.
Chelsea triumph in Wembley finale
Chelsea beat Aston Villa 1-0 in the last F.A Cup final at Wembley before the stadium was closed for reconstruction. Robert di Matteo, who had scored in the 1997 final, scored the only goal of the 2000 final to give Chelsea their third F.A Cup triumph and end Villa's hopes of winning the trophy for the first time since 1957.
O'Neill lured to Celtic
Martin O'Neill guided Leicester City to their second League Cup triumph in four seasons before moving north of the border to Celtic, whose 'dream team' partnership of Director of Football Kenny Dalglish and Head Coach John Barnes had ended a nightmare as they finished 22 points behind champions Rangers in the SPL title race and had suffered a shock SFA Cup exit at the hands of Inverness Caledonian Thistle, which had inspired The Sun newspaper headline: Super Caley Go Ballistic, Celtic Are Atrocious.
England blow it at Euro 2000
England overcame Scotland in the qualification playoffs to qualify for Euro 2000, and beat Germany in the group stages. But they surrendered two-goal leads to lose 3-2 to both Portugal and Romania and failed to reach the quarter finals. This dismal showing saw continued calls for the F.A to terminate Kevin Keegan's contract.
Veteran Robson takes over on Tyneside
Bobby Robson, 66, became the oldest manager ever to take charge of a Premiership club when he succeeded 37-year-old Ruud Gullit as manager of Newcastle United.
Chester out, Kidderminster in
Chester City were relegated to the Conference after 69 years of Football League membership. They were replaced by Conference champions Kidderminster Harriers, who had won the Conference title six years earlier but had been refused promotion because their Aggborough ground did not meet capacity requirements.
Coppell quits Palace again
Steve Coppell was sacked as Crystal Palace manager, having been in charge of the club four times in 16 years. New owner Simon Jordan brought in Alan Smith (who had managed Palace between 1993 and 1995) as Coppell's successor. The change of hands gave Palace fans hope for the future after a financial crisis had almost put the club out of business.
Shearer quits the international stage
Alan Shearer retired from international football after playing for England at Euro 2000, much to the dismay of many fans who felt that he still had a few years left in him at the highest level.
Wimbledon's luck finally runs out
Wimbledon were relegated from the Premiership after 14 years in the top flight. Their fate was sealed on 14th May, 12 years to the day that they had achieved their famous F.A Cup victory over Liverpool.
Leeds United's exciting 22-year-old Australian midfielder Harry Kewell was voted PFA Young Player of the Year after helping secure a Champions League place for his side.
Kevin Phillips opened his Premiership goalscoring account at Sunderland with 30 goals in a season - making him the highest scoring footballer in the whole league.
David O'Leary ended his first full season as Leeds United manager with a run to the semi finals of the UEFA Cup and qualification for next season's Champions League.
Alan Curbishley guided Charlton Athletic to promotion back to the Premiership at the first attempt after they finished champions of Division One.
George Burley finally got Ipswich Town into the Premiership when they triumphed in the Division One playoffs after three successive seasons of failure.
David Moyes continued Preston North End's revival by guiding them to title success in Division Two.
Stan Ternent guided Burnley to runners-up spot in Division Two and secured their promotion to Division One.
John Hollins brought success to Swansea City, who won the Division Three title.
Biggest rise
Gillingham won the Division Two playoffs to reach the upper half of the English league for the first time in their history.
Biggest fall
Wimbledon were relegated from the Premiership after 14 successive seasons of top flight football. 12 years earlier they had been F.A Cup winners.
25 August1999 — Kevin Phillips and Niall Quinn plunge Newcastle United into crisis as they score in Sunderland's 2-1 derby win at St. James' Park, leading to the resignation of Newcastle manager Ruud Gullit on 28 August, after just twelve months in charge. Newcastle have failed to win any of their opening five games so far in the season.
3 September1999 — Newcastle United appoint Bobby Robson as their new manager. The former England manager, 66, is the oldest manager in all four division of the English league - and almost 30 years older than his predecessor Ruud Gullit.
17 November1999 — Arsenal announce plans to move to a new 60,000-seat stadium at Ashburton Grove near Highbury - their home since 1913. They hope to be in their new home for the 2003-04 season.
19 April2000 — Manchester United surrender their defence of the European Cup after losing 3-2 at home to Real Madrid in the quarter final second leg.
22 April2000 — Manchester United secure their sixth Premier League title in eight seasons thanks to a 4-2 win at Southampton.
7 May2000 — Chester City are relegated to the Football Conference after 69 years of Football League membership. On the same day, Manchester City secure promotion to the Premier League as Division One runners-up (their second successive promotion), Walsall suffer relegation to Division Two, Burnley secure promotion to Division One as Division Two runners-up, and Northampton seal the third and final automatic promotion place in Division Three. Chester City's place in the Football League will be taken by Conference champions Kidderminster Harriers.
9 May2000 — Sheffield Wednesday are relegated from the Premier League after nine successive seasons of top flight football.
23 December1999: Stan Flashman, 69, rescued near-bankrupt non-league Barnet with a takeover deal in 1985. He made funds available to manager Barry Fry in hope of building a quality side, and this paid off with promotion to the Football League in 1991, but he had quit within two years with the club knee deep in financial problems once again. Although Flashman's rash attitude (which saw him sack and reinstate Fry eight times) made him unpopular with most Barnet fans, it is unlikely that Barnet would have experienced league football without his takeover — they could well have gone out of business.
24 February2000: Sir Stanley Matthews, 85, one of the greatest footballers England ever produced, died in his native Stoke-on-Trent three weeks after his 85th birthday. Despite his on-the-field brilliance, he only ever won one major trophy - the 1953 FA Cup with Blackpool. That game was dubbed 'The Matthews Final' because he had so influenced his side's dramatic recovery from almost certain defeat at the hands of Bolton Wanderers.
14 April2000: Wilf Mannion, 81, died just a few weeks after his old England team mate Sir Stanley Matthews. Mannion had played 26 times for England in the immediate postwar years, and was a regular goalscorer for Middlesbrough at club level.
Hasselbaink moved from Leeds United to Atletico Madrid in August 1999 for £12 million and then transferred again from Atletico to Chelsea in June 2000 for £15 million.