The season marked the beginning of the regular trend for clubs to leave their homes of many years and head for purpose built new stadia, following the bold move to Glanford Park by Scunthorpe United in 1988.

6 July 1989 – After just four months at Glasgow Rangers, Mel Sterland leaves the Scottish league champions and returns to England in a move to Second Division Leeds United for £600,000.

15 July 1989 – Laurie Cunningham, who played in Wimbledon's FA Cup triumph 14 months ago and had a successful spell with West Bromwich Albion in the late 1970s, dies in a car crash in Spain.

[1] 15 September 1989 – Queens Park Rangers pay £175,000 for Oxford United defender David Bardsley, with striker Mark Stein moving to the Manor Ground in exchange.

2 December 1989 - Liverpool remain top of the First Division on goal difference with a 4–1 win over Manchester City at Maine Road, which keeps the hosts at the bottom of the table.

[25] 3 December 1989 - Arsenal draw level on points with Liverpool at the top of the First Division when a Perry Groves goal gives them a 1–0 home win over Manchester United.

Aston Villa's title hopes are hit by a 2–0 defeat at Millwall, who are now needing the points to stay clear of the relegation zone after topping the table in September.

23 December 1989 - The last league action before Christmas sees Manchester United hold Liverpool to a goalless draw at Anfield, ensuring that Arsenal remain a point ahead at the top of the table with a game in hand.

[29] 26 December 1989 - The Boxing Day action sees Liverpool return to the top of the First Division with a 2–1 win over Sheffield Wednesday at Anfield, as Arsenal lose 1–0 at Southampton.

20-year-old striker Mark Robins scores his first goal for Manchester United in a 2–2 draw at Wimbledon, which rescues a point for Alex Ferguson's team but extend their winless run to six matches.

1 January 1990 - The new decade begins with Arsenal beating Crystal Palace 4–1 at Highbury to cut Liverpool's lead at the top of the First Division, as Kenny Dalglish's men are held to a 2–2 at the City Ground by Nottingham Forest.

[33] 7 January 1990 – Manchester United beat Nottingham Forest 1–0 at the City Ground in the third round of the FA Cup, with Mark Robins scoring the winning goal.

[35] 28 January 1990 - A Clayton Blackmore goal gives Manchester United a 1–0 win their FA Cup fourth round tie with Hereford at Edgar Street.

[40] 11 February 1990 - Nottingham Forest move closer to a joint record fourth League Cup triumph by beating Coventry 2–1 in the semi-final first leg at the City Ground.

13 February 1990 – Millwall, still battling relegation despite having led the First Division five months ago, sack manager John Docherty and his assistant Frank McLintock.

14 February 1990 – Oldham Athletic defeat West Ham United 6–0 at Boundary Park in the first leg of their League Cup semi–final, all but guaranteeing their first ever Wembley appearance.

[42] 16 February 1990 – Striker Tony Cascarino pledges his future to relegation threatened Millwall despite reports that he is to join Aston Villa or Manchester United.

14 March 1990 – First Division leaders Aston Villa suffer a shock 3–0 defeat at Oldham Athletic in the FA Cup quarter–finals, while Liverpool's double bid remains on course after a 1–0 replay win over Queens Park Rangers.

17 March 1990 - Aston Villa remain top of the table with a 1–0 win at Derby, extending their lead over Liverpool to five points, although the Reds have two games in hand.

[52] 31 March 1990 – Liverpool return to the top of the First Division at the end of the month, leading the table on goal difference with a game in hand ahead of Aston Villa.

[54] 8 April 1990 – Liverpool's hopes of a unique second double are ended when they lose 4–3 after extra time to Crystal Palace in the semi–finals of the FA Cup at Villa Park.

The game is however marred by controversy after referee Joe Worrall fails to award Oldham an early goal after Nick Henry's shot clearly crosses the line.

[56] 17 April 1990 – 20–year–old striker Mark Robins scores twice in Manchester United's 2–0 home league win over Aston Villa – a result which puts the opposition's title hopes into serious doubt.

Luton keep their survival bid alive with a 2–0 home win over Arsenal, while Sheffield Wednesday are still in danger of going down with a 1–0 defeat to QPR at Loftus Road.

Newcastle's 2–1 home win over West Ham keeps them in the hunt for automatic promotion, while leaving the visiting side's playoff hopes hanging by a thread.

[63] 5 May 1990 – Sheffield Wednesday are relegated on goal difference behind Luton Town, who win their final game of the season 3–2 at Derby County while the Hillsborough club lose 3–0 at home to Nottingham Forest.

21 May 1990 – 34 Bolton Wanderers hooligans who were convicted of taking part in attacks on police officers and rival supporters are banned from travelling to Italy for the duration of the World Cup by the Italian government.

[1] Alex Ferguson silenced the critics who attacked him for a lack of progress in the league by guiding Manchester United to a 1–0 replay victory over Crystal Palace in the FA Cup final, which was achieved after a 3–3 draw.

The pivotal game in his side's season had been in the televised third round tie at Nottingham Forest, when a Mark Robins goal gave relegation-threatened United a surprise win and triggered improved times for the club.

Nottingham Forest retained the Football League Cup to match the record of four wins in the competition set by Liverpool, while Manchester United, despite experiencing their worst league campaign since returning to the top-flight in 1975, finally won some silverware at the fourth attempt under Alex Ferguson by lifting the FA Cup to match the record of seven wins in the competition set by Aston Villa and Tottenham Hotspur.