The 1988–89 FA Cup was the 108th season of the world's oldest football knockout competition, the Football Association Challenge Cup, or FA Cup for short. Liverpool defeated Everton 3–2 in the final.
Qualifying rounds Most participating clubs that were not members of the Football League competed in the qualifying rounds to secure one of 28 places available in the first round.
The winners from the fourth qualifying round were Frickley Athletic, Southport, Barrow, Runcorn, Brandon United, Guisborough Town, Northwich Victoria, Altrincham, Halesowen Town, Dagenham, Welling United, Grays Athletic, Bromsgrove Rovers, Aylesbury United, Hayes, Woking, Stafford Rangers, Kettering Town, Hendon, Yeovil Town, Dartford, Waterlooville, Merthyr Tydfil, Sutton United, Fareham Town, Bognor Regis Town, Fisher Athletic and Newport County.
Guisborough Town was the only qualifying club appearing in the competition proper for the first time. Of the others, Brandon United had last featured at this stage in 1979–80, Barrow had last done so in 1976–77 and Grays Athletic had last done so in 1952–53.
Already experiencing acute financial difficulties when they were relegated from the Football League at the end of the previous season, Newport County was unable to recover in their first season of non-league competition since 1919–20. Defeated by eventual Football Conference champions Maidstone United in the first round of the FA Cup, County was wound up and disbanded in February 1989 with their final league record being expunged.
First round proper The 48 teams from the Football League Third and Fourth Divisions entered in this round along with the 28 non-league clubs from the qualifying rounds and Enfield, Telford United, Maidstone United and Bath City who were given byes. 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. Brandon United and Guisborough Town, from the Northern League at Step 8 of English football, were the lowest-ranked teams in the round.
Tie noHome teamScoreAway teamDate1Enfield (5)1–1Leyton Orient19 November 1988ReplayLeyton Orient2–2Enfield23 November 1988ReplayLeyton Orient0–1Enfield28 November 19882Blackpool2–1Scunthorpe United19 November 19883Darlington1–2Notts County19 November 19884Bath City (6)2–0Grays Athletic (6)19 November 19885Bristol City3–1Southend United19 November 19886Burnley0–2Chester City19 November 19887Preston North End1–1Tranmere Rovers19 November 1988ReplayTranmere Rovers3–0Preston North End22 November 19888Yeovil Town (5)3–2Merthyr Tydfil (6)19 November 19889Reading4–2Hendon (6)19 November 198810Woking (7)1–4Cambridge United19 November 198811Gillingham3–3Peterborough United19 November 1988ReplayPeterborough United1–0Gillingham23 November 198812Bolton Wanderers0–0Chesterfield19 November 1988ReplayChesterfield2–3Bolton Wanderers28 November 198813Grimsby Town1–0Wolverhampton Wanderers19 November 198814Stafford Rangers (5)2–2Crewe Alexandra19 November 1988ReplayCrewe Alexandra3–2Stafford Rangers22 November 198815Scarborough2–1Stockport County19 November 198816Doncaster Rovers0–0Brandon United (8)19 November 1988ReplayDoncaster Rovers2–1Brandon United22 November 198817Fulham0–1Colchester United19 November 198818Brentford2–0Halesowen Town (7)19 November 198819Bristol Rovers3–0Fisher Athletic (5)20 November 198820Altrincham (5)3–2Lincoln City19 November 198821Bognor Regis Town (6)2–1Exeter City19 November 198822Huddersfield Town1–1Rochdale19 November 1988ReplayRochdale3–4Huddersfield Town28 November 198823Mansfield Town1–1Sheffield United19 November 1988ReplaySheffield United2–1Mansfield Town22 November 198824Cardiff City3–0Hereford United19 November 198825Halifax Town1–0York City19 November 198826Newport County (5)1–2Maidstone United (5)19 November 198827Southport (6)0–2Port Vale19 November 198828Runcorn (5)2–2Wrexham19 November 1988ReplayWrexham2–3Runcorn22 November 198829Torquay United2–2Fareham Town (6)19 November 1988ReplayFareham Town2–3Torquay United23 November 198830Kettering Town (5)2–1Dartford (6)19 November 198831Rotherham United3–1Barrow (6)19 November 198832Aldershot1–0Hayes (6)19 November 198833Dagenham (6)0–4Sutton United (5)19 November 198834Waterlooville (6)1–4Aylesbury United (5)19 November 198835Telford United (5)1–1Carlisle United19 November 1988ReplayCarlisle United4–1Telford United22 November 198836Swansea City3–1Northampton Town19 November 198837Frickley Athletic (6)0–2Northwich Victoria (5)19 November 198838Hartlepool United2–0Wigan Athletic19 November 198839Welling United (5)3–0Bromsgrove Rovers (6)19 November 198840Guisborough Town (8)0–1Bury19 November 1988
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. Step 6 sides Bath City, from the Southern League Premier Division, and Bognor Regis Town, from the Isthmian League Premier Division, were the lowest-ranked teams in the round.
Tie noHome teamScoreAway teamDate1Enfield (5)1–4Cardiff City11 December 19882Blackpool3–0Bury10 December 19883Bath City (6)0–0Welling United (5)10 December 1988ReplayWelling United3–2Bath City14 December 19884Yeovil Town (5)1–1Torquay United10 December 1988ReplayTorquay United1–0Yeovil Town14 December 19885Reading1–1Maidstone United (5)10 December 1988ReplayMaidstone United1–2Reading14 December 19886Bolton Wanderers1–2Port Vale10 December 19887Grimsby Town3–2Rotherham United10 December 19888Northwich Victoria (5)1–2Tranmere Rovers10 December 19889Scarborough0–1Carlisle United10 December 198810Doncaster Rovers1–3Sheffield United11 December 198811Aylesbury United (5)0–1Sutton United (5)10 December 198812Altrincham (5)0–3Halifax Town10 December 198813Bognor Regis Town (6)0–1Cambridge United10 December 198814Huddersfield Town1–0Chester City10 December 198815Runcorn (5)0–3Crewe Alexandra10 December 198816Kettering Town (5)2–1Bristol Rovers10 December 198817Aldershot1–1Bristol City10 December 1988ReplayBristol City0–0Aldershot13 December 1988ReplayAldershot2–2Bristol City20 December 1988ReplayBristol City1–0Aldershot22 December 198818Peterborough United0–0Brentford10 December 1988ReplayBrentford3–2Peterborough United14 December 198819Colchester United2–2Swansea City10 December 1988ReplaySwansea City1–3Colchester United13 December 198820Hartlepool United1–0Notts County10 December 1988
Third round proper
Teams from the Football League First and Second Divisions entered in this round. 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. The round featured three clubs from the Football Conference at Step 5 of English football: Welling United, Sutton United and Kettering Town.
Tie noHome teamScoreAway teamDate1Blackpool (3)0–1AFC Bournemouth (2)7 January 19892Sutton United (5)2–1Coventry City (1)7 January 19893Walsall (2)1–1Brentford (3)7 January 1989ReplayBrentford1–0Walsall10 January 19894Nottingham Forest (1)3–0Ipswich Town (2)7 January 19895Sheffield Wednesday (1)5–1Torquay United (4)7 January 19896Crewe Alexandra (4)2–3Aston Villa (1)7 January 19897Middlesbrough (1)1–2Grimsby Town (4)7 January 19898West Bromwich Albion (2)1–1Everton (1)7 January 1989ReplayEverton1–0West Bromwich Albion11 January 19899Sunderland (2)1–1Oxford United (2)7 January 1989ReplayOxford United2–0Sunderland11 January 198910Derby County (1)1–1Southampton (1)7 January 1989ReplaySouthampton1–2Derby County10 January 198911Shrewsbury Town (2)0–3Colchester United (4)7 January 198912Tranmere Rovers (4)1–1Reading (3)7 January 1989ReplayReading2–1Tranmere Rovers11 January 198913Newcastle United (1)0–0Watford (2)7 January 1989ReplayWatford2–2Newcastle United10 January 1989ReplayNewcastle United0–0Watford16 January 1989ReplayWatford1–0Newcastle United18 January 198914Manchester City (2)1–0Leicester City (2)7 January 198915Barnsley (2)4–0Chelsea (2)7 January 198916Portsmouth (2)1–1Swindon Town (2)7 January 1989ReplaySwindon Town2–0Portsmouth10 January 198917West Ham United (1)2–2Arsenal (1)8 January 1989ReplayArsenal0–1West Ham United11 January 198918Brighton & Hove Albion (2)1–2Leeds United (2)7 January 198919Manchester United (1)0–0Queens Park Rangers (1)7 January 1989ReplayQueens Park Rangers2–2Manchester United11 January 1989ReplayManchester United3–0Queens Park Rangers23 January 198920Plymouth Argyle (2)2–0Cambridge United (4)7 January 198921Bradford City (2)1–0Tottenham Hotspur (1)7 January 198922Millwall (1)3–2Luton Town (1)7 January 198923Carlisle United (4)0–3Liverpool (1)7 January 198924Huddersfield Town (3)0–1Sheffield United (3)7 January 198925Cardiff City (3)1–2Hull City (2)7 January 198926Port Vale (3)1–3Norwich City (1)8 January 198927Charlton Athletic (1)2–1Oldham Athletic (2)7 January 198928Kettering Town (5)1–1Halifax Town (4)7 January 1989ReplayHalifax Town2–3Kettering Town10 January 198929Stoke City (2)1–0Crystal Palace (2)7 January 198930Birmingham City (2)0–1Wimbledon (1)7 January 198931Hartlepool United (4)1–0Bristol City (3)7 January 198932Welling United (5)0–1Blackburn Rovers (2)7 January 1989
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. Sutton United and Kettering Town were again the lowest-ranked teams in the round, and they were also the last non-league clubs left in the competition.
Tie noHome teamScoreAway teamDate1Watford2–1Derby County28 January 19892Nottingham Forest2–0Leeds United28 January 19893Blackburn Rovers2–1Sheffield Wednesday28 January 19894Aston Villa0–1Wimbledon28 January 19895Grimsby Town1–1Reading28 January 1989ReplayReading1–2Grimsby Town1 February 19896Swindon Town0–0West Ham United28 January 1989ReplayWest Ham United1–0Swindon Town1 February 19897Sheffield United3–3Colchester United28 January 1989ReplayColchester United0–2Sheffield United31 January 19898Brentford3–1Manchester City28 January 19899Manchester United4–0Oxford United28 January 198910Norwich City8–0Sutton United (5)28 January 198911Plymouth Argyle1–1Everton28 January 1989ReplayEverton4–0Plymouth Argyle31 January 198912Bradford City1–2Hull City28 January 198913Millwall0–2Liverpool29 January 198914Charlton Athletic2–1Kettering Town (5)28 January 198915Stoke City3–3Barnsley28 January 1989ReplayBarnsley2–1Stoke City31 January 198916Hartlepool United1–1AFC Bournemouth28 January 1989ReplayAFC Bournemouth5–2Hartlepool United31 January 1989
Fifth round proper
The fifth set of games were played over the weekend 18–19 February 1989, with replay being played on 22 February. Fourth Division side Grimsby Town was the lowest-ranked team in the draw.
Tie noHome teamScoreAway teamDate1AFC Bournemouth1–1Manchester United18 February 1989ReplayManchester United1–0AFC Bournemouth22 February 19892Watford0–3Nottingham Forest19 February 19893Blackburn Rovers0–2Brentford18 February 19894Barnsley0–1Everton18 February 19895Norwich City3–2Sheffield United18 February 19896Hull City2–3Liverpool18 February 19897Wimbledon3–1Grimsby Town18 February 19898Charlton Athletic0–1West Ham United18 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 was the last club from the First Round left in the competition, but their 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.