First round proper
The first round of games were played over the weekend 19–20 November 1988, with most replays being played on 22–23 November. All other replays were played on 28 November.
Second round proper
The second round of games were played over 10–11 December 1988, with the first round of replays being played on 13–14 December. The Aldershot-Bristol City game went to two more replays.
Third round proper
The third round of games in the FA Cup were played over the weekend 7–8 January 1989, with the first set of replays being played on 10–11 January. Two games went to second replays, and one to a third replay.
Fourth round proper
The fourth round of games were played over the weekend 28–29 January 1989, with replays being played on 31 January – 1 February.
Fifth round proper
The fifth set of games were played over the weekend 18–19 February 1989, with replay being played on 22 February.
|Tie no||Home team||Score||Away team||Date|
|1||Bournemouth||1–1||Manchester United||18 February 1989|
|Replay||Manchester United||1–0||Bournemouth||22 February 1989|
|2||Watford||0–3||Nottingham Forest||19 February 1989|
|3||Blackburn Rovers||0–2||Brentford||18 February 1989|
|4||Barnsley||0–1||Everton||18 February 1989|
|5||Norwich City||3–2||Sheffield United||18 February 1989|
|6||Hull City||2–3||Liverpool||18 February 1989|
|7||Wimbledon||3–1||Grimsby Town||18 February 1989|
|8||Charlton Athletic||0–1||West Ham United||18 February 1989|
Sixth round proper
Most of the sixth round of FA Cup games were played over the weekend 18–19 March 1989, with a replay on 22 March.
Third Division Brentford's impressive cup run was ended by a 4-0 defeat at Liverpool, who were chasing the double.
Wimbledon's defence of the trophy ended with a 1-0 defeat at Everton.
West Ham United, struggling in the league but thriving in the cup competitions (as League Cup semi-finalists), surrendered their chances of FA Cup glory with a 3-1 replay defeat to Norwich City following a goalless draw in the first game.
Nottingham Forest kept their outside chances of a unique domestic treble alive by winning 1-0 against Manchester United, who threw away their own last chance of silverware in a season where they had surprisingly failed to feature in the title race.
|Tie no||Home team||Score||Away team||Date|
|1||Liverpool||4–0||Brentford||18 March 1989|
|2||Everton||1–0||Wimbledon||19 March 1989|
|3||West Ham United||0–0||Norwich City||18 March 1989|
|Replay||Norwich City||3–1||West Ham United||22 March 1989|
|4||Manchester United||0–1||Nottingham Forest||18 March 1989|
- Main article: Hillsborough disaster
The FA Cup semi-finals were scheduled for 15 April 1989. The Everton–Norwich City game was completed as expected; however, the Liverpool–Nottingham Forest game was abandoned after six minutes due to the Hillsborough Disaster which claimed 94 lives on 15 April 1989 (the final death toll was 96). There was talk that the competition for this season would be abandoned, but on 30 April, it was confirmed that both teams would continue in the competition and play in a rescheduled semi-final, which was replayed on 7 May and won 3–1 by Liverpool.
Norwich's hopes of a first-ever FA Cup final were ended as Everton beat them 1–0 to book the second all-Merseyside FA Cup final in four seasons.
| 15 April 1989||Liverpool|| 0 – 0 |
|Nottingham Forest|| Hillsborough Stadium, Sheffield|
| 7 May 1989||Liverpool||3 – 1||Nottingham Forest|| Old Trafford, Manchester|
Referee: Ray Lewis
| Aldridge 3', 58' |
Laws 72' (o.g.)
| 15 April 1989||Everton||1 – 0||Norwich City|| Villa Park, Birmingham|
- Main article: 1989 FA Cup Final
The second all-Merseyside FA Cup final in four seasons ended like the previous one, with Liverpool beating Everton and Ian Rush scoring twice, although this time the scoreline was 3–2 rather than 3–1.
A fourth-minute goal from John Aldridge handed the initiative to Liverpool, but a late equaliser by Stuart McCall forced extra-time. Ian Rush restored Liverpool's lead five minutes into extra time, before Stuart McCall's second goal drew the scores level after 102 minutes. However, a second goal from Ian Rush came just two minutes later, and the trophy went to Anfield.
As a tribute to the fans who had died in the Hillsborough disaster, both teams wore black armbands and observed a minute's silence prior to the match.
| 20 May 1989|
|Everton|| Wembley Stadium, London|
Referee: Joe Worrall
| Aldridge 4'|
Rush 95', 104'
|McCall 89', 102'|
The BBC had all rights to show FA Cup games. They were able to show one live game from Round 3 onwards as part of Match of the Day Live. They were also able to show highlights of games from Round 1 onwards on Match Of The Day. These matches were.
|First round proper|| Enfield v Leyton Orient 1|
Southport v Port Vale 1
|Second round proper|| Kettering Town v Bristol Rovers|
Altrincham v Halifax Town1
|Third round proper||West Ham United v Arsenal 1|| Sutton United v Coventry City1|
Bradford City v Tottenham Hotspur1
West Bromwich Albion v Everton1
Port Vale v Norwich City
Manchester United v Queen's Park Rangers (Replay)
|Fourth round proper||Millwall v Liverpool 1||Norwich City v Sutton United1|
Charlton Athletic v Kettering Town
Aston Villa v Wimbledon1
Plymouth Argyle v Everton
|Fifth round proper||Watford v Nottingham Forest1||Hull City v Liverpool1|
Barnsley v Everton1
AFC Bournemouth v Manchester United
Wimbledon v Grimsby Town
Norwich City v Sheffield United1
|Sixth round proper||Everton v Wimbledon 1||Manchester United v Nottingham Forest1|
Liverpool v Brentford1
West Ham United v Norwich City
|Semi-finals||Liverpool v Nottingham Forest1|
|Final||Liverpool v Everton 1|
1Footage available on YouTube
Match of the Day was due to show highlights of both FA Cup Semi Finals, but this was cancelled due to the Hillsborough disaster.