The 2008–09 FA Cup (known as the FA Cup sponsored by E.ON for sponsorship reasons) was the 128th season of the world's oldest football knockout competition; the FA Cup. A record 762 clubs were accepted for the competition; one club, South Normanton Athletic, folded before the fixtures were released, leaving 761 clubs to appear in the draw. Two more clubs, Brierley Hill & Withymoor and Stapenhill, folded after the draws for the early rounds were made, giving their opponents a walkover.

The competition started on 16 August 2008 with the Extra preliminary round and concluded on 30 May 2009 with the Final, held at Wembley Stadium. Because winners Chelsea qualified for the 2009–10 UEFA Champions League by finishing 3rd in the 2008–09 Premier League, losing finalists Everton qualified for the play-off round of the 2009–10 UEFA Europa League. Because Everton also happened to qualify for a Europa League berth by finishing 5th in the Premier League, that berth was awarded to the 6th place team (Aston Villa), whose berth (which was available because 2009–10 Football League Cup winners Manchester United qualified for the Champions League as Premier League winners) was in turn awarded to the 7th place team (Fulham).

Premier League side Portsmouth were the defending champions, but were elimated in the fourth round by Swansea City.

This season's competition saw the beginning of a new television contract for the tournament, with ITV and Setanta Sports taking over the domestic rights from the BBC and Sky Sports, however this would prove to be the only season in which Setanta broadcast the competition, as it went into administration and closed down a few weeks after the final.

Calendar Round Main date Number of fixtures Clubs New entries this round Prize money Player of the Round Extra preliminary round 16 August 2008 203 761 → 558 406: 356th–761st £750 n/a Preliminary round 30 August 2008 166 558 → 392 129: 227th–355th £1,500 n/a First round qualifying 13 September 2008 116 392 → 276 66: 161st–226th £3,000 Derren Ibrahim (Dartford) Second round qualifying 27 September 2008 80 276 → 196 44: 117th–160th £4,500 Dean Lodge (Kingstonian) Third round qualifying 11 October 2008 40 196 → 156 none £7,500 Craig Davis (AFC Totton) Fourth round qualifying 25 October 2008 32 156 → 124 24: 93rd–116th £12,500 Sam Hatton (AFC Wimbledon) First round proper 8 November 2008 40 124 → 84 48: 45th–92nd £20,000 Jon Adams (AFC Telford United) Second round proper 29 November 2008 20 84 → 64 none £30,000 Lindon Meikle (Eastwood Town) Third round proper 3 January 2009 32 64 → 32 44: 1st–44th £75,000 Nathan Tyson (Nottingham Forest) Fourth round proper 24 January 2009 16 32 → 16 none £100,000 Scott Parker (West Ham United) Fifth round proper 14 February 2009 8 16 → 8 none £200,000 Mikel Arteta (Everton) Sixth round proper 7 March 2009 4 8 → 4 none £400,000 Robin van Persie (Arsenal) Semi-finals 18 April 200919 April 2009 2 4 → 2 none Winners: £1,000,000Losers: £500,000 Phil Jagielka (Everton) Final 30 May 2009 1 2 → 1 none Winner: £2,000,000Loser: £1,000,000

Qualifying rounds All teams that entered the competition, but were not members of the Premier League or The Football League, had to compete in the qualifying rounds to secure one of 32 places available in the first round proper.

The winners from the fourth qualifying round were Curzon Ashton, Kettering Town, Barrow, Kidderminster Harriers, Cambridge United, Altrincham, Droylsden, Histon, Alfreton Town, Blyth Spartans, Mansfield Town, AFC Telford United, Fleetwood Town, Eastwood Town, Stevenage Borough, Brackley Town, Ebbsfleet United, Oxford United, AFC Wimbledon, Team Bath, Dorchester Town, Eastbourne Borough, Forest Green Rovers, Bury Town, Harlow Town, Grays Athletic, Evesham United, Sutton United, Torquay United, Leiston, Havant & Waterlooville and AFC Hornchurch. These teams came from the following levels:

14 teams from Level 5 (Conference National) 9 from Level 6: 5 Conference North, 4 Conference South 6 from Level 7: 1 Northern Premier League, 2 Southern League, 3 Isthmian League 2 from Level 8: Curzon Ashton of the NPL North and Bury Town of the Southern League Midland 1 from Level 9: Leiston of the Eastern Counties League Premier Division

Three 'phoenix' clubs were appearing in the main draw for the first time: AFC Telford United reached this stage four years after the demise of the original Telford United F.C., AFC Wimbledon were here four years after Wimbledon F.C. became Milton Keynes Dons and AFC Hornchurch qualified for the main draw three years after the demise of the original Hornchurch F.C. Of the other teams, Curzon Ashton, Brackley Town, Evesham United and Leiston were also appearing in the competition proper for the first time while Dorchester Town had last done so in 2000-01, Eastwood Town had last done so in 1999-2000, Blyth Spartans had last done so in 1997-98, Sutton United in 1995-96, Harlow Town in 1991-92 and Bury Town in 1968-69.

First round proper All of the 24 League One and 24 League Two teams entered in this round, along with the winners of the previous round, the fourth qualifying round.

The draw took place on 26 October 2008. The matches were played between 7 and 9 November 2008.

Tie noHome teamScoreAway teamAttendance1Colchester United (3)0 – 1Leyton Orient (3)4,6002Havant & Waterlooville (6)1 – 3Brentford (4)1,6313Blyth Spartans (6)3 – 1Shrewsbury Town (4)2,7424Sutton United (7)0 – 1Notts County (4)2,0415Torquay United (5)2 – 0Evesham United (7)2,2756Oxford United (5)0 – 0Dorchester Town (6)3,196replayDorchester Town (6)1 – 3†Oxford United (5)1,4747Bury (4)0 – 1Gillingham (4)2,1618AFC Wimbledon (6)1 – 4Wycombe Wanderers (4)4,5289Chester City (4)0 – 3Millwall (3)1,93210Carlisle United (3)1 – 1Grays Athletic (5)3,921replay‡Grays Athletic (5)0 – 2Carlisle United (3)1,21711Team Bath (6)0 – 1Forest Green Rovers (5)90612Eastbourne Borough (5)0 – 0Barrow (5)1,216replayBarrow (5)4 – 0Eastbourne Borough (5)2,13113AFC Hornchurch (7)0 – 1Peterborough United (3)3,00014Yeovil Town (3)1 – 1Stockport County (3)3,582replayStockport County (3)5 – 0Yeovil Town (3)3,26015Leiston (9)0 – 0Fleetwood Town (6)1,250replayFleetwood Town (6)2 – 0Leiston (9)2,01016Accrington Stanley (4)0 – 0Tranmere Rovers (3)2,126replayTranmere Rovers (3)1 – 0Accrington Stanley (4)2,56017Walsall (3)1 – 3Scunthorpe United (3)2,31818AFC Bournemouth (4)1 – 0Bristol Rovers (3)3,93519Brighton & Hove Albion (3)3 – 3Hartlepool United (3)2,545replayHartlepool United (3)2 – 1Brighton & Hove Albion (3)3,28820Aldershot Town (4)1 – 1Rotherham United (4)2,632replayRotherham United (4)0 – 3Aldershot Town (4)2,431Tie noHome teamScoreAway teamAttendance21Morecambe (4)2 – 1Grimsby Town (4)1,71322Huddersfield Town (3)3 – 4Port Vale (4)6,94223Alfreton Town (6)4 – 2Bury Town (8)1,06024Kidderminster Harriers (5)1 – 0Cambridge United (5)1,71725Leicester City (3)3 – 0Stevenage Borough (5)7,58626Milton Keynes Dons (3)1 – 2Bradford City (4)5,54227Darlington (4)0 – 0Droylsden (6)2,479replayDroylsden (6)1 – 0Darlington (4)1,67228Chesterfield (4)3 – 1Mansfield Town (5)6,61229AFC Telford United (6)2 – 2Southend United (3)3,631replaySouthend United (3)2 – 0AFC Telford United (6)4,41530Curzon Ashton (8)3 – 2Exeter City (4)1,25931Histon (5)1 – 0Swindon Town (3)1,54132Kettering Town (5)1 – 1Lincoln City (4)3,314replayLincoln City (4)1 – 2Kettering Town (5)3,95333Barnet (4)1 – 1Rochdale (4)1,782replayRochdale (4)3 – 2†Barnet (4)2,33934Hereford United (3)0 – 0Dagenham & Redbridge (4)1,825replayDagenham & Redbridge (4)2 – 1Hereford United (3)1,40935Cheltenham Town (3)2 – 2Oldham Athletic (3)2,585replayOldham Athletic (3)0 – 1Cheltenham Town (3)2,55236Luton Town (4)0 – 0Altrincham (5)3,200replayAltrincham (5)0 – 0Luton Town (4)2,397Luton Town won 4–2 on penalties37Crewe Alexandra (3)1 – 0Ebbsfleet United (5)2,59338Eastwood Town (7)2 – 1Brackley Town (7)96039Leeds United (3)1 – 1Northampton Town (3)9,531replayNorthampton Town (3)2 – 5Leeds United (3)3,96040Harlow Town (7)0 – 2Macclesfield Town (4)2,149

† – After extra time

‡ – Grays' replay with Carlisle was abandoned the first time it was played after 20 minutes because of floodlight failure with Grays leading 1–0.

Blyth Spartans, Droylsden and Histon beat teams from two levels higher. Kettering Town were the fourth non-league team to beat a league club. Curzon Ashton were the only club to beat a team from four levels higher, beating Exeter City.

Second round proper The draw was held on 9 November 2008 and involved the 40 winning teams from the previous round. These were from the following levels:

13 from Level 3 (League One) 14 from Level 4 (League Two) 7 from Level 5 (Conference National) 4 from Level 6 (all Conference North) 1 from Level 7 (Eastwood Town of the Northern Premier League Premier Division) 1 from Level 8 (Curzon Ashton of the Northern Premier League North)

The draw was conducted by Lawrie Sanchez and Ray Parlour. Matches in the second round proper were played over the weekend of 29 November 2008, with the exception of the match between Crewe Alexandra and Carlisle United, which was played on 3 December, due to the abandonment of the first-round game between Carlisle United and Grays Athletic.

Tie noHome teamScoreAway teamAttendance1‡Chesterfield (4)2 – 2Droylsden (6)5,698replay‡Droylsden (6)2 – 1Chesterfield (4)2,824Droylsden expelled for fielding an ineligible player; Chesterfield progress2Peterborough United (3)0 – 0Tranmere Rovers (3)5,980replayTranmere Rovers (3)1 – 2†Peterborough United (3)3,1393Eastwood Town (7)2 – 0Wycombe Wanderers (4)1,9554Notts County (4)1 – 1Kettering Town (5)4,451replayKettering Town (5)2 – 1Notts County (4)3,0195Leicester City (3)3 – 2Dagenham & Redbridge (4)7,7916Barrow (5)2 – 1Brentford (4)3,5327Bradford City (4)1 – 2Leyton Orient (3)5,0658Southend United (3)3 – 1Luton Town (4)4,1119Forest Green Rovers (5)2 – 0Rochdale (4)1,71510Histon (5)1 – 0Leeds United (3)4,10311Scunthorpe United (3)4 – 0Alfreton Town (6)4,24912Torquay United (5)2 – 0Oxford United (5)2,64713Fleetwood Town (6)2 – 3Hartlepool United (3)3,28014Morecambe (4)2 – 3Cheltenham Town (3)1,75815Gillingham (4)0 – 0Stockport County (3)4,419replayStockport County (3)1 – 2Gillingham (4)3,32916Millwall (3)3 – 0Aldershot Town (4)6,15917Carlisle United (3)0 – 2Crewe Alexandra (3)2,75518AFC Bournemouth (4)0 – 0Blyth Spartans (6)4,165replayBlyth Spartans (6)1 – 0AFC Bournemouth (4)4,04019Kidderminster Harriers (5)2 – 0Curzon Ashton (8)2,07020Port Vale (4)1 – 3Macclesfield Town (4)4,684

† – After extra time

‡ – Droylsden's first visit to Chesterfield was abandoned at half time due to fog. The first replay, two weeks later, was then abandoned after 70 minutes due to floodlight failure.

6 non-league clubs beat league clubs: Leeds United lost to Histon, while League Two clubs lost to Eastwood Town, Blyth Spartans, Barrow, Forest Green Rovers and Kettering Town.

Third round proper The draw was held on 30 November 2008. The draw was carried out by Sir Trevor Brooking and Ray Clemence at Soho Square. The 20 Premier League and 24 Championship teams enter at this stage, along with the 20 winners from the previous round. These 20 teams came from the following levels:

9 from Level 3 (League One) 3 from Level 4 (League Two) 6 from Level 5 (Conference National) 1 from Level 6 (Blyth Spartans of the Conference North) 1 from Level 7 (Eastwood Town of the Northern Premier League Premier Division)

The matches were played between 2 and 5 January 2009, with the exception of the ties between Birmingham City and Wolverhampton Wanderers, Histon and Swansea City, Cheltenham Town and Doncaster Rovers, and Leyton Orient and Sheffield United, which were postponed until 13 January 2009.