Their absence meant that in the 3rd round of the competition, there was an uneven number of teams, and so Darlington were picked out of a hat of "lucky losers" and played against Aston Villa despite having lost in the 2nd round of the competition. 28 August 1999 – Ruud Gullit resigns after one year as manager of Newcastle United.

Blackpool had been coping well in previous seasons despite financial problems, but they finally took their toll this season and helped send the club down. [23], 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. League One 1999/2000 results page on FlashScore.com offers results, League One 1999/2000 standings and match details. Chelsea beat Aston Villa 1–0 in the last FA Cup final at Wembley before its redevelopment.

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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. 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. 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. In the end Chester, who had spent virtually the entire season rooted to the bottom of the table and only had the chance of a last-day escape because of similarly poor campaigns by Carlisle and Shrewsbury, were relegated to the Conference. 3 September 1999 – Newcastle United appoint Bobby Robson as their new manager. 7 March 2000 – John Hartson's proposed move from Wimbledon to Tottenham Hotspur collapses after he fails a medical. 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. Scunthorpe, who had won promotion via the play-offs the previous year, never achieved enough wins to have a serious chance of survival, and went straight back down. -1999: 2000-2004: 2005-2009: 2010-now . A Premier League thriller at Upton Park sees West Ham United beat Bradford City 5–4.