[18] 23 August 1988 – Kevin Moran leaves Manchester United on a free transfer after ten years and joins Spanish side Sporting Gijón.

Forwards John Aldridge, Alan Smith, and Tony Cottee score opening day hat-tricks as Liverpool beat Charlton Athletic 3–0, Arsenal move to top position by thrashing FA Cup holders Wimbledon 5–1, while Everton thump Newcastle United 4–0.

[20] Tottenham Hotspur's opening fixture at home to Coventry City was postponed following the Londoners' failure to obtain a safety certificate for White Hart Lane.

1 September 1988 – Brighton & Hove Albion, newly promoted back to the Second Division, sign Barnet defender Nicky Bissett for £115,000, a record fee for a non-league player.

17 September – Southampton drop points for the first time this season with a 2–2 draw against Arsenal at Highbury, enabling Norwich to go top with a 2–0 win at Newcastle, who go bottom of the table.

[35] 13 October 1988 – Ron Atkinson steps down as West Bromwich Albion manager for the second time, taking over at Atlético Madrid in Spain, in a contract worth £250,000 per year.

[47] 31 October 1988 – Norwich City are back at the top of the First Division table at the end of the month, now with a six-point lead over nearest rivals Arsenal, who have a game in hand, while Millwall are still third.

[59] 25 November 1988 – Wimbledon defender Terry Phelan is omitted from tomorrow's squad for the First Division fixture against Liverpool due to a court appearance he faces on a charge of cannabis possession.

[63] 4 December 1988 – Newcastle United's search for a manager ends when they recruit Jim Smith from Queens Park Rangers,[64] who put coach Peter Shreeves in temporary charge of the first team.

Barnsley climb into the playoff zone and are in strong contention for a place in the top flight of English football for the first time, beating struggling Shrewsbury 3–2 at Gay Meadow.

20-year-old midfielder Russell Beardsmore, starting for only the second time in the league, scored a second half equaliser for United before setting up a goal each for Brian McClair and Mark Hughes to wipe out Liverpool's lead.

[81] 12 January 1989 – After just seven months at Newcastle United, goalkeeper Dave Beasant signs for Second Division leaders Chelsea in a £725,000 deal which contracts him to the Stamford Bridge club until 1994.

[85] 9 February 1989 – Nottingham Forest manager Brian Clough is fined £5,000 and banned from the touchline for the rest of the season for punching supporters who invaded the pitch in the recent League Cup quarter-final victory over Queens Park Rangers.

[86] 14 February 1989 – Just three months after quitting West Bromwich Albion to take over at Spanish side Atlético Madrid, Ron Atkinson returns to England to succeed Peter Eustace as manager of First Division strugglers Sheffield Wednesday.

[90] 24 February 1989 – Roy Hattersley, deputy Labour Party leader, warns that the Conservative government's proposed ID card scheme will increase violence outside football grounds.

[81] 21 March 1989 – Fourth Division strugglers Stockport County sack player-manager Asa Hartford and replace him with Rochdale manager Danny Bergera.

[98][99] 22 March 1989 – Norwich City move closer to their first-ever FA Cup final by defeating West Ham United 3–1 in the quarter-final replay at Carrow Road.

[100] West Ham United also break their transfer fee record by paying £1.1million to bring striker Frank McAvennie back to the club after 18 months at Celtic.

[20] Chelsea have returned to the top of the Second Division, exchanging places with Manchester City, while the play-off zone is occupied by West Bromwich Albion, Blackburn Rovers, Ipswich Town and AFC Bournemouth.

[106] 5 April 1989 – Newport County lose a final appeal against their closure in the High Court more than a month ago; they are expelled from the GM Vauxhall Conference and their record for the season is expunged.

15 April 1989 – English football endures its greatest ever tragedy with the death of 94 Liverpool supporters, and injury of some 300 others, at the FA Cup semi-final clash with Nottingham Forest at Hillsborough.

[20] 17 April 1989 – Within 48 hours of the tragedy at Hillsborough, Home Secretary Douglas Hurd promises to pass new legislation which will force all Football League teams to remove standing accommodation from their stadiums.

19 April 1989 – The Sun newspaper posts a front-page article about the Hillsborough disaster, headlined "The Truth", with lurid and untrue allegations about Liverpool fans' conduct,[110][111] from sources including South Yorkshire Police and Conservative MP Irvine Patnick.

[113] 28 April 1989 – Of the 25 Liverpool fans who were extradited in connection with the Heysel disaster of May 1985, in which 39 spectators died at the European Cup final, 14 are found guilty of voluntary manslaughter; they went on to serve one year in prison.

[20] Maidstone United clinch the Conference title and are promoted to the Football League, giving them a clash next season with fellow Kent club Gillingham, who are relegated to the Fourth Division on the same day.

Kenny Sansom leaves Newcastle United to return to London in an exchange deal to Queens Park Rangers, with Wayne Fereday moving in the opposite direction.

3 June 1989 – The domestic season draws to a close when Crystal Palace overhaul a 3–1 deficit to defeat Blackburn Rovers 4–3 on aggregate to win promotion to the First Division after an eight-year exile.

[118] 5 June 1989 – John Lyall, the longest-serving manager currently employed in the Football League, is sacked after 15 years in charge of relegated West Ham United.

Brian Clough's Nottingham Forest ended their nine-year trophy drought by beating holders Luton Town 3–1 in the final to win the League Cup.

1 April 1989: David May, 18-year-old defender, makes his debut for Blackburn Rovers in a 1–1 Second Division draw with fellow promotion rivals Swindon Town at the County Ground.