17 June 1999 –
David James leaves
Liverpool after seven years in a £1.7 million move to
Aston Villa. 21 June 1999 – The
France national team captain
Didier Deschamps joins
Chelsea in a £3 million move from
Juventus. 30 June 1999 –
Bradford City prepare for their first time top division season for nearly 80 years with a club record £1.4 million move for
Leeds United defender
David Wetherall. 5 July 1999 – Chelsea pay a club record £10 million for
Blackburn Rovers striker
Chris Sutton. 14 July 1999 –
Newcastle United pay
Ipswich Town £6.5 million for midfielder
Kieron Dyer and
Everton pay
Trabzonspor £3 million for on-loan striker
Kevin Campbell, who scored eight goals in seven games for them late last season. 23 July 1999 – Leeds United sign striker
Michael Bridges from
Sunderland for £5 million. 29 July 1999 – Four years after leaving
Arsenal,
Stefan Schwarz returns to English football in a £4 million move to Sunderland from
Valencia. 31 July 1999 –
Middlesbrough sign
German international midfielder
Christian Ziege from
AC Milan for £4 million. 1 August 1999 – Arsenal lift the
Charity Shield thanks to a 2–1 victory over
Manchester United at
Wembley. 2 August 1999 – Arsenal sell
Nicolas Anelka to
Real Madrid for £23 million – the highest fee involving a British club. 3 August 1999 – Arsenal sign
Thierry Henry for an estimated fee of £11 million, reuniting with his former manager
Arsène Wenger. 4 August 1999 – Leeds United sell
Jimmy Floyd Hasselbaink to
Atlético Madrid of Spain for £12 million. 7 August 1999 –
Wigan Athletic mark their first game at the
JJB Stadium with a 3–0 win over
Scunthorpe United in
Division Two. The first Premier League games of the season include Chelsea's 4–0 home win over newly-promoted Sunderland and
Watford's 3–2 home defeat against
Wimbledon in their return to the top flight. Bradford City mark their first top-flight game since 1922 with a 1–0 away win over
Middlesbrough, in which
Dean Saunders scores a late winner. 10 August 1999 –
Kevin Phillips scores his first two Premier League goals in Sunderland's 2–0 home win over his old club Watford. 11 August 1999 – Manchester United beat
Sheffield Wednesday 4–0 at
Old Trafford.
Michael Bridges scores a hat-trick for Leeds United in their 3–0 away win over Southampton. Leeds United sign
Coventry City striker
Darren Huckerby for £4.4 million. 14 August 1999 –
Tommy Mooney scores for Watford in their shock 1–0 league win at Liverpool. 18 August 1999 – 19-year-old
Wolverhampton Wanderers striker
Robbie Keane becomes Coventry City's record signing in a £6 million deal. 21 August 1999 – Manchester United captain
Roy Keane scores twice in a 2–1 win over Arsenal at
Highbury. 25 August 1999 – Kevin Phillips and
Niall Quinn plunge Newcastle United into crisis as they score in Sunderland's 2–1 derby win at St. James' Park, 27 August 1999 –
Lazio beat Manchester United 1–0 in
Monaco to win the
European Super Cup. 28 August 1999 –
Ruud Gullit resigns after one year as manager of Newcastle United. 30 August 1999 –
Andy Cole scores four goals against his old club Newcastle United as Manchester United beat them 5–1 at Old Trafford. 31 August 1999 – The first month of the league season ends with treble winners Manchester United looking well placed for retaining their league title as Premier League leaders with five wins and a draw from their first six games. Aston Villa are their nearest contenders, while Chelsea, West Ham United and Leicester City complete the top five. Sheffield Wednesday and Newcastle United, both winless, prop up the rest of the top flight, while Bradford City occupy the final bottom three position at the end of the first month of their first top division season for nearly 80 years. Ipswich Town are hopeful of making it back to the Premier League after five seasons away (during which time they have suffered three play-off disappointments) as they finish the first month of the season as Division One leaders.
Stockport County have emerged as surprise contenders for a Premier League place as they stand second in Division One. The playoff zone is occupied by
West Bromwich Albion,
Manchester City,
Birmingham City and
Fulham. 3 September 1999 – 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. 7 September 1999 –
Ade Akinbiyi becomes the most expensive Division Two player when he leaves
Bristol City for Division One promotion hopefuls Wolverhampton Wanderers. 11 September 1999 –
Jamie Carragher scores two own goals as Liverpool lose 3–2 at home to Manchester United in the league. 17 September 1999 – Former England and
Liverpool full-back
Rob Jones retires from football at the age of 28 after failing to recover from a succession of injuries. 18 September 1999 – Newcastle United record the second highest win in
FA Premier League history when they beat Sheffield Wednesday 8–0.
Alan Shearer scores five goals in this game, while Kevin Phillips scores a hat-trick in Sunderland's 5–0 win at Derby County. In a rare appearance for Manchester United,
Jordi Cruyff scores a late equaliser in their 1–1 home draw with Wimbledon. 30 September 1999 – Manchester United retain their lead of the Premier League, with Leeds United now their nearest contenders by a two-point margin. Arsenal, Sunderland and Chelsea complete the top five. Sheffield Wednesday remain bottom after a terrible first two months of the season, while Newcastle United remain second from bottom despite that record-breaking victory 12 days ago, and Wimbledon now occupy the final remaining relegation position. Ipswich Town and Birmingham City are level on points at the top of Division One.
Charlton Athletic, Manchester City, Fulham and
Barnsley complete the top six. 2 October 1999 – Sheffield Wednesday record a 5–1 home win over Wimbledon. 3 October 1999 – Chelsea crush Manchester United 5–0 – the first domestic competitive game that United have lost for nearly nine months.
Alan Shearer scores twice as Newcastle beat Middlesbrough 2–1. 24 October 1999 – A Premier League thriller at
Goodison Park sees Everton and Leeds United draw 4–4, a result that ends the Yorkshire club's 10-match winning streak. Elsewhere, a late
Trevor Sinclair equalizer for West Ham United stops ten-man Sunderland's ascension to the top; the Black Cats instead rise to third. 31 October 1999 – October draws to a close with Leeds United as the new Premier League leaders, with Manchester United in second place and trailing them by two points. Arsenal, Sunderland and Leicester City complete the top five. Sheffield Wednesday remain bottom, with Watford and Bradford City completing the bottom three. Manchester City lead Division One, with Ipswich Town, Charlton Athletic and Birmingham City level on points as their nearest rivals.
Huddersfield Town and Fulham complete the top six. 13 November 1999 –
Paul Scholes scores twice as
England beat
Scotland 2–0 at
Hampden Park in the
Euro 2000 qualifying playoff first leg. 17 November 1999 — England qualify for Euro 2000 despite a 1–0 second leg defeat by Scotland at Wembley. Manchester City remain top of Division One, with Huddersfield Town now second and in the hunt for top division for the first time in nearly 30 years. Charlton Athletic, Ipswich Town, Barnsley and Fulham occupy the playoff places. 1 December 1999 – Film producer and actor
Bill Kenwright, 54, completes a takeover of
Everton after buying out former owner
Peter Johnson. 4 December 1999 –
Ole Gunnar Solskjaer scores four goals in Manchester United's 5–1 home league win over Everton. 31 December 1999 – 1999 draws to a close and as the new millennium approaches, Leeds United are back on top though with just a one-point lead over Manchester United who have a game in hand. Arsenal, Sunderland and Liverpool are the only three teams still posing a reasonable threat to the top two. Sheffield Wednesday's terrible season has continued as they remain bottom with a mere two wins and nine points from their first 20 games, while Watford and Derby County remain in the bottom three. The race for promotion to the Premier League is still headed by Manchester City and Huddersfield Town, while Charlton Athletic, Ipswich Town, Barnsley and Stockport County complete the top six. 8 January 2000 – Liverpool suffer a shock 1–0 home defeat to Blackburn Rovers in the FA Cup fourth round. Tranmere Rovers, on a good run in the League Cup, progress to the fifth round of the FA Cup after a surprise 1–0 win at home to Sunderland in the fourth round. There is a major shock also for Bradford City, who are crushed 3–1 by Division Two Gillingham at
Priestfield. 12 January 2000 – Liberian striker
George Weah, 31, joins Chelsea on a six-month loan from
A.C. Milan. 19 January 2000 – Arsenal's hopes of FA Cup glory are ended in a replay penalty shoot-out defeat by Leicester City, who boost their own bid for a cup double. 29 January 2000 – The FA Cup fifth round brings some surprise results as Gillingham's giant-killing run continues with a 3–1 home win over Sheffield Wednesday and Charlton Athletic win at Coventry City to give the rest of the Premier League some idea of what they will be performing like when inevitable promotion is achieved. Leicester City's hopes of a domestic cup double are ended when they lose 2–1 at Chelsea, while Cambridge United's impressive run ends in a 3–1 home defeat by Bolton Wanderers. On the transfer front, Division One strugglers West Bromwich Albion sell their Italian midfielder
Enzo Maresca to
Juventus for £4 million. 30 January 2000 –
Blackpool striker
Martin Aldridge, 25, on loan to
Rushden & Diamonds, dies in an
Oxford hospital after being injured in a car crash in
Northamptonshire. 31 January 2000 – Struggling Sheffield Wednesday complete the month unbeaten in the
FA Premier League.
Danny Wilson is named
FA Premier League Manager of the Month, but the club are still in the relegation zone, though no longer in the bottom place (now occupied by Watford. Bradford City occupy the other relegation position. Manchester United now lead at the top on goal difference ahead of Leeds United, with Arsenal and Liverpool still posing a threat but Sunderland's challenge is ebbing away. Charlton Athletic have taken over from Manchester City as Division One leaders. Ipswich Town, Barnsley, Huddersfield Town and Wolverhampton Wanderers complete the top six. 12 February 2000 – Manchester United suffer their first Premier League defeat in four months, and only their third of the season, as they lose 3–0 at Newcastle United. A Premier League thriller at
Upton Park sees West Ham United beat Bradford City 5–4. 19 February 2000 – Bolton Wanderers reach the FA Cup semi-finals with a 1–0 win over Charlton Athletic as they hope to challenge for a "Wembley double" of the FA Cup final and Division One play-off final. 20 February 2000 – Gillingham's FA Cup dreams are ended with a 5–0 defeat at Chelsea, while a 2–1 defeat at home to Aston Villa resigns Everton to another season of disappointment in
Walter Smith's second season as manager. Tranmere Rovers are eliminated by Newcastle United after a brave 3–2 defeat. 23 February 2000 –
Stanley Matthews, one of the greatest English footballers of all time, dies at the age of 85. 26 February 2000 – Wimbledon become the first team this season to be unbeaten twice in the league by Manchester United after holding them to a 2–2 draw at
Selhurst Park. 29 February 2000 – Manchester United have now extended their Premier League lead to six points as February ends, with Leeds United posing the closest threat, while Arsenal and Liverpool (along with a resurgent Chelsea) pose a more distant threat, and Sunderland are now focused on qualifying for the
UEFA Cup rather than challenging for the league title. Sheffield Wednesday and Watford continue to prop up the Premier League, with Bradford City joining them in the drop zone. Charlton Athletic and Manchester City continue to head the Division One promotion race, with Ipswich Town, Barnsley, Huddersfield Town and Birmingham City completing the top six. 4 March 2000 – Debutant striker
Stan Collymore scores a hat-trick for
Leicester City in their 5–2 win over
Sunderland in the Premier League, just days after his transfer from
Aston Villa. 7 March 2000 –
John Hartson's proposed move from
Wimbledon to
Tottenham Hotspur collapses after he fails a medical. 10 March 2000 – Liverpool pay a club record £11 million for Leicester City striker
Emile Heskey. 11 March 2000 –
Steffen Iversen scores a hat-trick in Tottenham's 7–2 home league win over Southampton. 22 March 2000 –
Dean Windass scores a hat-trick in Bradford City's 4–4 relegation crunch thriller with Derby County at
Valley Parade. 31 March 2000 – Manchester United are now looking all set for title glory as they head the table by a seven-point margin with Leeds United as their closest rivals. Liverpool, Chelsea and Arsenal are looking more and more distant a threat in the race to prevent the Premier League trophy from remaining at
Old Trafford. At the other end of the table, Sheffield Wednesday and Watford are looking doomed, with Bradford City occupying the final relegation position and Derby County hovering dangerously close to the drop zone. The race for Premier League football next season is headed by Charlton Athletic and Ipswich Town. Barnsley, Manchester City, Huddersfield Town and Birmingham City complete the top six. 2 April 2000 – Aston Villa beat Bolton Wanderers on penalties after a goalless draw in the FA Cup semi-final at Wembley, to reach their first FA Cup final for 43 years. 5 April 2000 – Two Leeds United Fans, Chris Loftus and Kevin Speight are killed on the eve of the club's UEFA Cup Semi-final against Galatasaray. 9 April 2000 – Two goals from
Gus Poyet give Chelsea a 2–1 win over Newcastle United in the FA Cup semi-final. 10 April 2000 – A late surge by Middlesbrough is unable to prevent Manchester United from winning a thrilling Premier League 4–3 at the
Riverside Stadium. 15 April 2000 – All Premier League matches kicked off at 3.06 pm, to commemorate the 96 Liverpool supporters who lost their lives in the
Hillsborough disaster. 19 April 2000 – Derby County bring
Georgi Kinkladze back to England after two years with
Ajax after agreeing a £3 million deal. Manchester United surrender their defence of the
European Cup after losing 3–2 at home to
Real Madrid in the quarter-final second leg. 21 April 2000 – Charlton Athletic win promotion back to the Premier League after one season away. 22 April 2000 – Manchester United seal their sixth Premier League title in eight seasons with a 3–1 win at Southampton. 29 April 2000 – Bradford City boost their survival bid and dent Wimbledon's with a 3–0 win at Valley Parade. 30 April 2000 – April draws to a close with champions Manchester United an incredible 19 points ahead of second placed Arsenal, who have two games in hand. Liverpool are looking set for the third Champions League place, while Chelsea head the UEFA Cup race. Leeds United meanwhile have fallen to fifth place after a disastrous run of results, and now look unlikely to even qualify for European competition at all. Aston Villa, Sunderland and West Ham United remain in with a slim chance of taking the league's UEFA Cup slot. Charlton Athletic have been confirmed as Division One champions, but the race for second place is still being contested by Manchester City and Ipswich Town. 7 May 2000 –
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 May 2000 – Sheffield Wednesday are relegated from the Premier League after nine successive seasons of top-flight football, but go down fighting with a 3–3 draw against Arsenal. 14 May 2000 – Wimbledon lose 2–0 at Southampton and are relegated to
Division One after 14 years in the top flight, and 12 years to the day after their FA Cup triumph over Liverpool. Bradford City, meanwhile, confirm their survival with a 1–0 win over Liverpool, who surrender a Champions League place to Leeds United. 14 May 2000 –
ITV announces a £500 million bid to bring live
Premier League matches onto terrestrial television for the first time. If the deal goes ahead, it will be the first time since 1992 (when the Premier League was created from the old
Football League First Division) that live top division football has been shown on any terrestrial television channel. 18 May 2000 – West Ham United sell
Marc-Vivien Foé to
Olympique Lyonnais for £6 million. 20 May 2000 –
Chelsea beat
Aston Villa 1–0 in the last FA Cup final to be played at
Wembley before the 77-year-old stadium is rebuilt.
Roberto Di Matteo, who scored for Chelsea in the opening minute of their 1997 triumph, scores the only goal of the game. 29 May 2000 –
Ipswich Town seal promotion to the Premier League after a five-year exile by defeating
Barnsley 4–2 in the Division One playoff final at Wembley. It is their first win at Wembley since they won the FA Cup in 1978. 30 May 2000 – Arsenal sign
Cameroon defender
Lauren for £7.2 million from
Mallorca. 31 May 2000 – Manchester United pay a national record fee for a goalkeeper when they sign
AS Monaco and France goalkeeper
Fabien Barthez for £7.8 million. 1 June 2000 –
Martin O'Neill leaves
Leicester City to take over as manager of
Celtic. Tottenham Hotspur pay a club record £11 million for
Dynamo Kyiv striker
Serhii Rebrov. 2 June 2000 – Chelsea equal the national transfer record (set by
Alan Shearer four years ago) with a £15 million move for Jimmy Floyd Hasselbaink. 14 June 2000 –
Match of the Day, the longest-running and most popular football programme on British television, is set to end after next season as a result of
ITV's £183 million deal to show highlights from Premier League games. 20 June 2000 – Chelsea sign
Icelandic striker
Eiður Guðjohnsen from Bolton Wanderers for £5 million. ==Women's football==