| Tournament details | |
|---|---|
| Country | England Wales |
| Final positions | |
| Champions | Chelsea(3rd title) |
| Runners-up | Aston Villa |
| Tournament statistics | |
| Top goal scorer(s) | Gustavo Poyet (6 goals) |
The1999–2000 FA Cup (known asThe FA Cup sponsored by AXA for sponsorship reasons) was the 119th staging of theFA Cup. Both the semifinals and final of the competition were played atWembley Stadium for the last time before reconstruction work began. The competition culminated with thefinal betweenChelsea andAston Villa. The game was won by a goal from Chelsea'sRoberto Di Matteo, giving them a 1–0 victory.
The title holdersManchester United, withdrew from the 1999–2000 competition due to their participation in the2000 FIFA Club World Championship inSouth America, to take place in early 2000,[1] thus becoming the first FA Cup winners not to defend their title. Despite this being at the request ofthe Football Association (FA), who believed the move would boost England's chances of winning the bid to host the2006 FIFA World Cup, they received criticism from journalists and television pundits.[2] To keep the competition running smoothly, the FA chose to draw one team from among those lower-division teams defeated in the second round to progress as "lucky losers" to the third.[3]Darlington were the team drawn.[4]
The main competition started in November 1999 for clubs from the Football League and Premiership.
| Round | Date | Matches | Clubs | New entries this round | Prize money |
|---|---|---|---|---|---|
| Preliminary round | 21 August 1999 | 166 | 558 → 392 | 161: 227th–387th | £1,000 |
| First round qualifying | 4 September 1999 | 116 | 392 → 276 | 66: 161st–226th | £2,250 |
| Second round qualifying | 18 September 1999 | 80 | 276 → 196 | 44: 117th–160th | £3,750 |
| Third round qualifying | 2 October 1999 | 40 | 196 → 156 | none | £5,000 |
| Fourth round qualifying | 16 October 1999 | 32 | 156 → 124 | 24: 93rd–116th | £10,000 |
| First round proper | 30 October 1999 | 40 | 124 → 84 | 48: 45th–92nd | £16,000 |
| Second round proper | 19 November 1999 | 20 | 84 → 64 | none | £24,000 |
| Third round proper | 11 December 1999 | 32 | 64 → 32 | 43: 2nd–44th‡ | £40,000 |
| Fourth round proper | 8 January 2000 | 16 | 32 → 16 | none | £60,000 |
| Fifth round proper | 29 January 2000 | 8 | 16 → 8 | none | £120,000 |
| Sixth round proper | 19 February 2000 | 4 | 8 → 4 | none | £300,000 |
| Semi-finals | 2 April 2000 | 2 | 4 → 2 | none | £900,000 |
| Final | 20 May 2000 | 1 | 2 → 1 | none | £1,000,000 |
‡ Manchester United, who were the winnersthe previous season, did not enter.
All participating clubs that were not members of thePremier League orFootball League entered the competition in the qualifying rounds to secure one of 32 places available in the first round proper.
The winners from the fourth qualifying round wereGuiseley,Eastwood Town,Gateshead,Doncaster Rovers,Tamworth,Hednesford Town,Southport,Morecambe,Stalybridge Celtic,Runcorn,Bamber Bridge,Worthing,Oxford City,Hendon,Whyteleafe,Merthyr Tydfil,Welling United,Hayes,Kingstonian,Rushden & Diamonds,Forest Green Rovers,Ilkeston Town,Yeovil Town,Bath City,Enfield,Chelmsford City,Aldershot Town,Burton Albion,Kettering Town,St Albans City,Hereford United andCambridge City.
Eastwood Town, Bamber Bridge, Whyteleafe and Forest Green Rovers were appearing in the competition proper for the first time. Aldershot Town was also appearing at this stage for the first time in their own right, seven years after the mid-season demise of the originalAldershot FC. Of the others, only Oxford City, who had last featured in the first round in1970-71, had not qualified for the main draw at least once in the last decade.
This is the first round in which teams from the Second and Third Divisions of the Football League compete with non-League teams.
| 30 October 1999 | Aldershot Town (6) | 1 – 1 | Hednesford Town (5) | Recreation Ground,Aldershot |
Abbott 56'Bentley  74'  Bassey 83' | Robinson 51' | Attendance: 3,269 Referee: G Hegley |
| 8 November 1999Replay | Hednesford Town (5) | 1 – 2 | Aldershot Town (6) | Keys Park,Hednesford |
| Lake 44' | Chewins 68' Abbott 87' | Attendance: G Hegley Referee: 1,719 |
| 31 October 1999 | Barnet (4) | 0 – 1 | Burnley (3) | Underhill Stadium,Barnet |
| Cook 74' | Attendance: 2,563 Referee:Rob Styles |
| 31 October 1999 | Bath City (6) | 0 – 2 | Hendon (6) | Twerton Park,Bath |
| Gentle 74' Genchev 90' | Attendance: 1,690 Referee: S Castle |
| 30 October 1999 | Blackpool (3) | 2 – 0 | Stoke City (3) | Bloomfield Road,Blackpool |
| Carlisle 5' Nowland 90' | Attendance: 4,721 Referee: D Laws |
| 30 October 1999 | Brentford (3) | 2 – 2 | Plymouth Argyle (4) | Griffin Park,London |
| Owusu 56' Marshall 63' | Stonebridge 43' McGregor 83' | Attendance: 4,287 Referee:Anthony Bates |
| 9 November 1999replay | Plymouth Argyle (4) | 2 – 1 (a.e.t.) | Brentford (3) | Home Park,Plymouth |
| McGregor 67',112' | Quinn 82' | Attendance: 5,409 Referee:Anthony Bates |
| 30 October 1999 | Bristol City (3) | 3 – 2 | Mansfield Town (4) | Ashton Gate,Bristol |
| Tinnion 44',50' Murray 65'Taylor 9' | Lormor 10' (pen.) Blake 89' | Attendance: 5,411 Referee: R Olivier |
| 31 October 1999 | Bristol Rovers (3) | 0 – 1 | Preston North End (3) | Memorial Stadium,Bristol |
| McKenna 52' | Attendance: 6,145 Referee: M J Brandwood |
| 30 October 1999 | Burton Albion (6) | 0 – 0 | Rochdale (4) | Eton Park,Burton upon Trent |
| Attendance: 3,103 Referee:Mark Halsey |
| 9 November 1999Replay | Rochdale (4) | 3 – 0 | Burton Albion (6) | Spotland,Rochdale |
| Platt 5' Peake 48'Dowe 82' | Attendance: 2,633 Referee:Mark Halsey |
| 30 October 1999 | Cambridge City (6) | 0 – 2 | Wigan Athletic (3) | City Ground,Cambridge |
| Barlow 30',44' | Attendance: 4,024 Referee: Steve Tomlin |
| 30 October 1999 | Cambridge United (3) | 1 – 0 | Gateshead (6) | Abbey Stadium,Cambridge |
| Taylor 79' | Fletcher 79' | Attendance: 2,970 Referee:Peter Walton |
| 30 October 1999 | Cheltenham Town (4) | 1 – 1 | Gillingham (3) | Whaddon Road,Cheltenham |
| Brough 77' | Southall 37' | Attendance: 3,188 Referee: Trevor Parkes |
| 9 November 1999Replay | Gillingham (3) | 3 – 2 | Cheltenham Town (4) | Priestfield Stadium,Gillingham |
| Thomson 24' Pennock 41'McGlinchey 77' | Milton 56' Howarth 70' | Attendance: 4,352 |
| 30 October 1999 | Chesterfield (3) | 1 – 2 | Enfield (6) | Saltergate,Chesterfield |
| Lomas 49' | Bunn 23' Brown 67' | Attendance: 2,506 Referee:Mark Warren |
| 30 October 1999 | Darlington (4) | 2 – 1 | Southport (5) | Feethams,Darlington |
| Tutill 35' Gabbiadini 77' (pen.) | Bolland 52' | Attendance: 4,313 Referee: S J Baines |
| 30 October 1999 | Doncaster Rovers (5) | 0 – 2 | Halifax Town (4) | Belle Vue,Doncaster |
| Tate 51' Paterson 82' | Attendance: 5,588 Referee:Graham Barber |
| 30 October 1999 | Exeter City (4) | 2 – 1 | Eastwood Town (7) | St James Park,Exeter |
| Flack 40' Gale 47'Bradley 65' | Smith 56' | Attendance: 2,441 Referee: S W Mathieson |
| 30 October 1999 | Forest Green Rovers (5) | 6 – 0 | Guiseley (6) | The Lawn Ground,Nailsworth |
| Hunt 1',31',62' McGregor 25'Drysdale 38'Sykes 51' | Hogarth 66' | Attendance: 1,047 Referee: M J Jones |
| 31 October 1999 | Hartlepool United (4) | 1 – 0 | Millwall (3) | Victoria Park,Hartlepool |
| Jones 90' | Attendance: 2,847 Referee: J A Kirkby |
| 30 October 1999 | Hayes (5) | 2 – 1 | Runcorn (6) | Church Road,Hayes |
| Bunce 25' Charles 90' | McDonald 45' | Attendance: 890 Referee:Phil Dowd |
| 30 October 1999 | Hereford United (5) | 1 – 0 | York City (4) | Edgar Street,Hereford |
| May 77' | Attendance: 2,787 Referee: M Cowburn |
| 30 October 1999 | Ilkeston Town (6) | 2 – 1 | Carlisle United (4) | New Manor Ground,Ilkeston |
| Moore 39' Raynor 62' | Harries 18' | Attendance: 1,748 Referee:Mike Dean |
| 30 October 1999 | Leyton Orient (4) | 1 – 1 | Cardiff City (3) | Brisbane Road,Leyton |
| Ampadu 56' Joseph 85' | Nugent 39' (pen.) | Attendance: 3,109 Referee: G Cain |
| 9 November 1999Replay | Cardiff City (3) | 3 – 1 | Leyton Orient (4) | Ninian Park,Cardiff |
| Brazier 22' Perrett 51'Nugent 54' | Smith 2' | Attendance: 3,095 Referee: G Cain |
| 30 October 1999 | Lincoln City (4) | 1 – 0 | Welling United (5) | Sincil Bank,Lincoln |
| Smith 30' | Attendance: 2,766 Referee:Richard Beeby |
| 30 October 1999 | Luton Town (3) | 4 – 2 | Kingstonian (5) | Kenilworth Road,Luton |
| Gray 11' George 66'Spring 76'Taylor 79' | Crossley 35' Leworthy 47' | Attendance: 4,682 Referee:Phil Joslin |
| 30 October 1999 | Macclesfield Town (4) | 0 – 0 | Hull City (4) | Moss Rose,Macclesfield |
| Attendance: 2,401 Referee: P R Richards |
| 9 November 1999Replay | Hull City (4) | 4 – 0 | Macclesfield Town (4) | Boothferry Park,Hull |
| Eyre 3',61' Greaves 7'Brown 29' | Attendance: 4,844 Referee: P R Richards |
| 2 November 1999 | Merthyr Tydfil (6) | 2 – 2 | Stalybridge Celtic (6) | Penydarren Park,Merthyr Tydfil |
| Mitchell 50',84' | Parr 9' Sullivan 42' | Attendance: 871 |
| 9 November 1999Replay | Stalybridge Celtic (6) | 3 – 1 | Merthyr Tydfil (6) | Bower Fold,Stalybridge |
| Bauress 2' (pen.) Pickford 24'Sullivan 86' | Lima 3' | Attendance: 1,399 |
| 30 October 1999 | Notts County (3) | 1 – 1 | AFC Bournemouth (3) | Meadow Lane,Nottingham |
| Rapley 17' | Warren 53' | Attendance: 3,674 Referee:Jeff Winter |
| 9 November 1999Replay | AFC Bournemouth (3) | 4 – 2 | Notts County (3) | Dean Court,Bournemouth |
| Fletcher 44' (67) Robinson 89' (pen.)Stein 89' | Redmile 78' Tierney 84' | Attendance: 4,026 Referee:Jeff Winter |
| 30 October 1999 | Oldham Athletic (3) | 4 – 0 | Chelmsford City (7) | Boundary Park,Oldham |
| Dudley 28' Sheridan 29'Duxbury 70'Whitehall 83' | Attendance: 4,392 Referee: A N Butler |
| 30 October 1999 | Oxford United (3) | 3 – 2 | Morecambe (5) | Manor Ground,Oxford |
| Lilley 12' Powell 58'Abbey 87' | Wright 28' Jackson 47' | Attendance: 3,504 Referee: A R Hall |
| 30 October 1999 | Peterborough United (4) | 1 – 1 | Brighton & Hove Albion (4) | London Road,Peterborough |
| Clarke 24' | Freeman 35' | Attendance: 7,260 Referee:Neale Barry |
| 9 November 1999Replay | Brighton & Hove Albion (4) | 3 – 0 | Peterborough United (4) | Withdean Stadium,Brighton |
| Rogers 9' Watson 63'Mayo 88' | Attendance: 5,612 Referee:Neale Barry |
| 30 October 1999 | Reading (3) | 4 – 2 | Yeovil Town (5) | Madejski Stadium,Reading |
| Bernal 31' Caskey 63' (pen.)Hunter 80'Williams 87' | Foster 36' Eaton 90' | Attendance: 8,032 Referee: Bill Jordan |
| 30 October 1999 | Rotherham United (4) | 3 – 0 | Worthing (7) | Millmoor,Rotherham |
| Thompson 31' Garner 81'Martindale 90' (pen.) | Attendance: 3,716 Referee: K Hill |
| 29 October 1999 | Rushden & Diamonds (5) | 2 – 0 | Scunthorpe United (3) | Nene Park,Irthlingborough |
| Warburton 48' Hamsher 76' (pen.) | Attendance: 4,112 Referee: G Stretton |
| 30 October 1999 | Shrewsbury Town (4) | 2 – 1 | Northampton Town (4) | Gay Meadow,Shrewsbury |
| Kerrigan 24' Wilding 70' | Hendon 43' | Attendance: 2,584 Referee: M Fletcher |
| 30 October 1999 | St Albans City (6) | 0 – 2 | Bamber Bridge (6) | Clarence Park,St Albans |
| Randall 90' | Whittaker 45' Carroll 89'Jones 59' Maddock 89' | Attendance: 1,127 Referee: B Curson |
| 30 October 1999 | Swansea City (4) | 2 – 1 | Colchester United (3) | Clarence Park,Swansea |
| Cusack 83' Watkin 89' | LuaLua 52' | Attendance: 3,622 Referee: R D Furnandiz |
| 30 October 1999 | Tamworth (6) | 2 – 2 | Bury (3) | The Lamb Ground,Tamworth |
| Haughton 8' Hallam 75' | Bullock 1' Littlejohn 68' | Attendance: 2,743 Referee: Alan Kaye |
| 9 November 1999Replay | Bury (3) | 2 – 1 (a.e.t.) | Tamworth (6) | Gigg Lane,Bury |
| Billy 86' James 95' | Haughton 15' | Attendance: 2,531 Referee: Alan Kaye |
| 30 October 1999 | Torquay United (4) | 1 – 0 | Southend United (4) | Plainmoor,Torquay |
| O'Brien 75' | Attendance: 2,520 Referee: L Cable |
| 30 October 1999 | Whyteleafe (7) | 0 – 0 | Chester City (4) | Church Road,Whyteleafe |
| Attendance: 2,164 Referee: P Taylor |
| 9 November 1999Replay | Chester City (4) | 3 – 1 | Whyteleafe (7) | Saunders Honda Stadium,Chester |
| Cross 25',52' Beckett 48' | Lunn 8' Thornton 45' | Attendance: 2,183 Referee: P Taylor |
| 30 October 1999 | Wrexham (3) | 1 – 1 | Kettering Town (5) | Racecourse Ground,Wrexham |
| Roberts 85' | Brown 48' | Attendance: 2,701 Referee:Alan Wiley |
| 10 November 1999Replay | Kettering Town (5) | 0 – 2 | Wrexham (3) | Nene Park,Irthlingborough |
| Roberts 11' Williams 22' | Attendance: 2,611 Referee:Alan Wiley |
| 30 October 1999 | Wycombe Wanderers (3) | 1 – 1 | Oxford City (7) | Adams Park,High Wycombe |
| Simpson 67' | Pierson 87' | Attendance: 2,963 Referee: P S Danson |
| 16 November 1999 | Oxford City (7) | 0 – 1‡ | Wycombe Wanderers (3) | Manor Ground,Oxford |
| Brown 51' | Attendance: 4,004 Referee: P S Danson |
‡ - Oxford City's replay with Wycombe Wanderers was abandoned after extra time due to a fire within the stadium. The score was 1–1.[5]
| Giantkiller(tier) | Opponent (tier) |
|---|---|
| Upset of two or more leagues above | |
| Enfield (level 6) | 2–1 away vsChesterfield (level 3) |
| Ilkeston Town (level 6) | 2–1 at home vsCarlisle United (level 4) |
| Rushden & Diamonds (level 5) | 2–0 at home vsScunthorpe United (level 3) |
| 20 November 1999 | Blackpool (3) | 2 – 0 | Hendon (6) | Bloomfield Road,Blackpool |
| Clarkson 69' Durnin 73' | Attendance: 2,975 Referee: K A Leach |
| 20 November 1999 | AFC Bournemouth (3) | 0 – 2 | Bristol City (3) | Dean Court,Bournemouth |
| Fletcher 71' | Murray 21',53' | Attendance: 5,223 Referee: Bill Jordan |
| 20 November 1999 | Burnley (3) | 2 – 0 | Rotherham United (4) | Turf Moor,Burnley |
| Cook 67' Mullin 75' | Attendance: 8,110 Referee: G Laws |
| 20 November 1999 | Bury (3) | 0 – 0 | Cardiff City (3) | Gigg Lane,Bury |
| Attendance: 2,603 Referee:Matt Messias |
| 30 November 1999Replay | Cardiff City (3) | 1 – 0 (a.e.t.) | Bury (3) | Ninian Park,Cardiff |
| Ford 120' | Attendance: 4,511 Referee:Matt Messias |
| 20 November 1999 | Cambridge United (3) | 1 – 0 | Bamber Bridge (6) | Abbey Stadium,Cambridge |
| Butler 71' (pen.) | Attendance: 3,303 Referee: W C Burns |
| 20 November 1999 | Exeter City (4) | 2 – 0 | Aldershot Town (6) | St James Park,Exeter |
| Alexander 32' Flack 35'Power 64' | Attendance: 4,151 Referee: C R Wilkes |
| 21 November 1999 | Forest Green Rovers (5) | 0 – 3 | Torquay United (4) | The Lawn Ground,Nailsworth |
| Brandon 77' Hill 81'Donaldson 87' | Attendance: 2,962 Referee:Phil Joslin |
| 20 November 1999 | Gillingham (3) | 3 – 1 | Darlington (4)† | Priestfield Stadium,Gillingham |
| Butters 17' Taylor 43',47' | Duffield 55' | Attendance: 5,168 Referee: P Jones |
| 20 November 1999 | Hayes (5) | 2 – 2 | Hull City (4) | Church Road,Hayes |
| Charles 21',63' (pen.) | Watts 4' (o.g.) Edwards 56'Brabin 63' | Attendance: 2,749 Referee: Steve Tomlin |
| 30 November 1999Replay | Hull City (4) | 3 – 2 (a.e.t.) | Hayes (5) | Boothferry Park,Hull |
| Brown 49' Edwards 97'Wood 112' | Gallen 78' Charles 114' | Attendance: 7,000 Referee: Steve Tomlin |
| 21 November 1999 | Hereford United (5) | 1 – 0 | Hartlepool United (4) | Edgar Street,Hereford |
| Elmes 54' | Attendance: 4,914 Referee: Anthony Leake |
| 20 November 1999 | Ilkeston Town (6) | 1 – 1 | Rushden & Diamonds (5) | New Manor Ground,Ilkeston |
| Eshelby 18' | de Souza 51' | Attendance: 2,737 Referee: A R Hall |
| 30 November 1999Replay | Rushden & Diamonds (5) | 3 – 0 | Ilkeston Town (6) | Nene Park,Irthlingborough |
| Wooding 2' Town 17'Collins 86' | Knapper 74' | Attendance: 4,226 Referee: A R Hall |
| 19 November 1999 | Luton Town (3) | 2 – 2 | Lincoln City (4) | Kenilworth Road,Luton |
| Doherty 63',84' | Gordon 14' Barnett 81' | Attendance: 4,291 Referee:Stephen Lodge |
| 30 November 1999Replay | Lincoln City (4) | 0 – 1 | Luton Town (3) | Sincil Bank,Lincoln |
| Douglas 85' | Attendance: 3,822 Referee:Stephen Lodge |
| 20 November 1999 | Oldham Athletic (3) | 1 – 0 | Swansea City (4) | Boundary Park,Oldham |
| Whitehall 45' | Attendance: 4,332 Referee: M Fletcher |
| 20 November 1999 | Plymouth Argyle (4) | 0 – 0 | Brighton & Hove Albion (4) | Home Park,Plymouth |
| Freeman 61' Cullip 76' | Attendance: 7,414 Referee:Rob Harris |
| 30 November 1999Replay | Brighton & Hove Albion (4) | 1 – 2 | Plymouth Argyle (4) | Withdean Stadium,Brighton |
| Cullip 63' | Bastow 9' Hargreaves 65' | Attendance: 5,710 Referee:Stephen Lodge |
| 20 November 1999 | Preston North End (3) | 0 – 0 | Enfield (6) | Deepdale,Preston |
| Attendance: 11,566 Referee: P Rejer |
| 30 November 1999Replay | Enfield (6) | 0 – 3 | Preston North End (3) | Clarence Park,St Albans |
| Protheroe 60' | Eyres 52' Alexander 60' (pen.)Gunnlaugsson 83' | Attendance: 1,808 Referee: P Rejer |
| 20 November 1999 | Reading (3) | 1 – 1 | Halifax Town (4) | Madejski Stadium,Reading |
| Caskey 75' (pen.) Parkinson 39' | Mitchell 60' | Attendance: 5,918 Referee:Richard Beeby |
| 30 November 1999Replay | Halifax Town (4) | 0 – 1 | Reading (3) | The Shay,Halifax |
| Caskey 74' (pen.) Polston 90' | Attendance: 2,156 Referee:Richard Beeby |
| 20 November 1999 | Shrewsbury Town (4) | 2 – 2 | Oxford United (3) | Gay Meadow,Shrewsbury |
| Kerrigan 8',54' | Murphy 63' Folland 77' | Attendance: 3,357 Referee: T Jones |
| 30 November 1999Replay | Oxford United (3) | 2 – 1 (a.e.t.) | Shrewsbury Town (4) | Manor Ground,Oxford |
| Murphy 90',117' | Jagielka 27' | Attendance: 4,096 Referee: T Jones |
| 20 November 1999 | Stalybridge Celtic (6) | 1 – 2 | Chester City (4) | Bower Fold,Stalybridge |
| Scott 8' Parr 90' | Cross 45' Beckett 69' | Attendance: 3,312 Referee: Michael Ryan |
| 20 November 1999 | Wrexham (3) | 2 – 1 | Rochdale (4) | Racecourse Ground,Wrexham |
| Roberts 5' Faulconbridge 88' | Atkinson 33' | Attendance: 3,408 Referee: Trevor Parkes |
| 20 November 1999 | Wycombe Wanderers (3) | 2 – 2 | Wigan Athletic (3) | Adams Park,High Wycombe |
| Devine 20' Ryan 90' | Haworth 45',61' | Attendance: 2,992 Referee: R Olivier |
| 30 November 1999Replay | Wigan Athletic (3) | 2 – 1 | Wycombe Wanderers (3) | JJB Stadium,Wigan |
| Liddell 28' Haworth 80' | Baird 23' | Attendance: 3,967 Referee: R Olivier |
^† = Darlington advanced aslucky losers
This round marked the first time First Division and Premier League (top-flight) teams played.
| 13 December 1999 | Arsenal (1) | 3 – 1 | Blackpool (3) | Highbury,London |
| Grimandi 23' Adams 65'Overmars 89' | Clarkson 38' | Attendance: 34,143 Referee:Uriah Rennie |
| 11 December 1999 | Aston Villa (1) | 2 – 1 | Darlington (4) | Villa Park,Birmingham |
| Carbone 43' Dublin 63' | Heckingbottom 71' | Attendance: 22,101 Referee: P R Richards |
| 21 December 1999 | Bolton Wanderers (2) | 1 – 0 | Cardiff City (3) | Reebok Stadium,Bolton |
| Guðjohnsen 29' | Attendance: 5,734 Referee: G Laws |
| 10 December 1999 | Cambridge United (3) | 2 – 0 | Crystal Palace (2) | Abbey Stadium,Cambridge |
| Benjamin 74' Wanless 81' | Mullins 84' | Attendance: 5,631 Referee: P Taylor |
| 11 December 1999 | Charlton Athletic (2) | 2 – 1 | Swindon Town (2) | The Valley,London |
| Kinsella 48',61' | Gooden 64' | Attendance: 10,939 Referee: A N Butler |
| 12 December 1999 | Chester City (4) | 1 – 4 | Manchester City (2) | Saunders Honda Stadium,Chester |
| Richardson 27' | Goater 19',90' Bishop 78'Doughty 90' (o.g.) | Attendance: 5,469 Referee: T Heilbron |
| 11 December 1999 | Crewe Alexandra (2) | 1 – 2 | Bradford City (1) | Alexandra Stadium,Crewe |
| Little 75' | Blake 53' Saunders 83' | Attendance: 6,571 Referee:Alan Wilkie |
| 11 December 1999 | Derby County (1) | 0 – 1 | Burnley (3) | Pride Park,Derby |
| Cooke 62' | Attendance: 23,400 Referee:Mike Riley |
| 11 December 1999 | Exeter City (4) | 0 – 0 | Everton (1) | St James Park,Exeter |
| Attendance: 6,045 Referee:Steve Bennett |
| 21 December 1999Replay | Everton (1) | 1 – 0 | Exeter City (4) | Goodison Park,Liverpool |
| Barmby 85' | Attendance: 16,869 Referee:Steve Bennett |
| 11 December 1999 | Fulham (2) | 2 – 2 | Luton Town (3) | Craven Cottage,London |
| Horsfield 11' Davis 14' | George 6' Spring 82' | Attendance: 8,251 Referee: G B Frankland |
| 21 December 1999Replay | Luton Town (3) | 0 – 3 | Fulham (2) | Kenilworth Road,Luton |
| Hayles 57',60' Hayward 63' | Attendance: 8,170 Referee: G B Frankland |
| 11 December 1999 | Grimsby Town (2) | 3 – 2 | Stockport County (2) | Blundell Park,Cleethorpes |
| Livingstone 57',60' Bradley Allen 63' | Attendance: 3,400 |
| 11 December 1999 | Hereford United (5) | 0 – 0 | Leicester City (1) | Edgar Street,Hereford |
| Attendance: 7,795 Referee:Mike Dean |
| 22 December 1999Replay | Leicester City (1) | 2 – 1 (a.e.t.) | Hereford United (5) | Filbert Street,Leicester |
| Elliott 78' Izzet 104' | Fewings 40' | Attendance: 12,157 Referee:Mike Dean |
| 12 December 1999 | Huddersfield Town (2) | 0 – 2 | Liverpool (1) | Alfred McAlpine Stadium,Huddersfield |
| Report | Camara 36' Matteo 59' | Attendance: 23,678 Referee:Rob Harris |
| 11 December 1999 | Hull City (4) | 1 – 6 | Chelsea (1) | Boothferry Park,Hull |
| Brown 38' | Poyet 8',49',58' Sutton 39'Di Matteo 47'Edwards 90' (o.g.) | Attendance: 10,279 Referee: P Jones |
| 13 December 1999 | Ipswich Town (2) | 0 – 1 | Southampton (1) | Portman Road,Ipswich |
| Richards 40' | Attendance: 14,383 Referee:Graham Barber |
| 12 December 1999 | Leeds United (1) | 2 – 0 | Port Vale (2) | Elland Road,Leeds |
| Bakke 61',68' | Attendance: 11,912 Referee:Steve Dunn |
| 11 December 1999 | Norwich City (2) | 1 – 3 | Coventry City (1) | Carrow Road,Norwich |
| Llewellyn 66' | Whelan 58' Roussel 76'Eustace 84' | Attendance: 15,702 Referee:Paul Alcock |
| 10 December 1999 | Nottingham Forest (2) | 1 – 1 | Oxford United (3) | City Ground,Nottingham |
| Llewellyn 66' | Whelan 58' | Attendance: 8,079 Referee:Andy D'Urso |
| 8 January 2000Replay | Oxford United (3) | 1 – 3 | Nottingham Forest (2) | Manor Ground,Oxford |
| Powell 72' Lundin | Bart-Williams 81',83' (pen.) Rogers 89' | Attendance: 7,191 Referee:Andy D'Urso |
| 11 December 1999 | Preston North End (3) | 2 – 1 | Oldham Athletic (3) | Deepdale,Preston |
| Macken 6' Alexander 69' (pen.) | Adams 85' Hotte 69' | Attendance: 9,940 Referee:Paul Danson |
| 11 December 1999 | Queens Park Rangers (2) | 1 – 1 | Torquay United (4) | Loftus Road,London |
| Wardley 9' | O'Brien 82' | Attendance: 8,843 Referee: K A Leach |
| 21 December 1999Replay | Torquay United (4) | 2 – 3 | Queens Park Rangers (2) | Plainmoor,Torquay |
| Bedeau 52' Thomas 80' | Wardley 56',74' Kiwomya 71' | Attendance: 5,232 Referee: K A Leach |
| 11 December 1999 | Reading (3) | 1 – 1 | Plymouth Argyle (4) | Madejski Stadium,Reading |
| McIntyre 37' | Hargreaves 82' | Attendance: 8,536 Referee:Alan Wiley |
| 21 December 1999Replay | Plymouth Argyle (4) | 1 – 0 | Reading (3) | Home Park,Plymouth |
| Heathcote 88' | Smith 39' | Attendance: 8,965 Referee:Alan Wiley |
| 12 December 1999 | Sheffield United (2) | 1 – 1 | Rushden & Diamonds (5) | Bramall Lane,Sheffield |
| Bent 14' | Brady 45' | Attendance: 10,104 Referee: B Knight |
| 21 December 1999Replay | Rushden & Diamonds (5) | 1 – 1 (a.e.t.) (5-6p) | Sheffield United (2) | Nene Park,Irthlingborough |
| Warburton 105' | Derry 103' | Attendance: 6,010 Referee: B Knight |
| 11 December 1999 | Sheffield Wednesday (1) | 1 – 0 | Bristol City (3) | Hillsborough,Sheffield |
| Booth 24' Quinn 90' | Attendance: 11,644 Referee: M Reed |
| 11 December 1999 | Sunderland (1) | 1 – 0 | Portsmouth (2) | Stadium of Light,Sunderland |
| McCann 24' | Panopoulos 40' | Attendance: 26,535 Referee:Neale Barry |
| 12 December 1999 | Tottenham Hotspur (1) | 1 – 1 | Newcastle United (1) | White Hart Lane,London |
| Iversen 57' | Speed 77' | Attendance: 33,116 Referee:Graham Poll |
| 22 December 1999Replay | Newcastle United (1) | 6 – 1 | Tottenham Hotspur (1) | St James' Park,Newcastle |
| Speed 5' Dabizas 27'Ferguson 45'Dyer 73'Shearer 83' (pen.),85' | Ginola 34' | Attendance: 35,415 Referee:Graham Poll |
| 11 December 1999 | Tranmere Rovers (2) | 1 – 0 | West Ham United (1) | Prenton Park,Birkenhead |
| Henry 21' | Attendance: 13,629 Referee:Dermot Gallagher |
| 11 December 1999 | Walsall (2) | 1 – 1 | Gillingham (3) | Bescot Stadium,Walsall |
| Robins 75' (pen.) | Southall 27' | Attendance: 4,314 Referee:Eddie Wolstenholme |
| 8 January 2000Replay | Gillingham (3) | 2 – 1 (a.e.t.) | Walsall (2) | Priestfield Stadium,Gillingham |
| Barras 38' (o.g.) Thomson 100' | Lárusson 44' | Attendance: 6,538 Referee:Eddie Wolstenholme |
| 11 December 1999 | Watford (1) | 0 – 1 | Birmingham City (2) | Vicarage Road,Watford |
| Rowett 66' | Attendance: 8,144 Referee:Paul Durkin |
| 11 December 1999 | West Bromwich Albion (2) | 2 – 2 | Blackburn Rovers (2) | The Hawthorns,West Bromwich |
| Hughes 66' Evans 80' | Frandsen 65' Blake 70' | Attendance: 10,609 Referee:Rob Styles |
| 22 December 1999Replay | Blackburn Rovers (2) | 2 – 0 (a.e.t.) | West Bromwich Albion (2) | Ewood Park,Blackburn |
| Duff 94' Carsley 114' (pen.) | Attendance: 11,766 Referee:Rob Styles |
| 11 December 1999 | Wigan Athletic (3) | 0 – 1 | Wolverhampton Wanderers (2) | JJB Stadium,Wigan |
| Robinson 90' | Attendance: 10,531 Referee: C Wilkes |
| 11 December 1999 | Wimbledon (1) | 1 – 0 | Barnsley (2) | Selhurst Park,London |
| Cort 34' | Attendance: 4,505 Referee:Mark Halsey |
| 11 December 1999 | Wrexham (3) | 2 – 1 | Middlesbrough (1) | Racecourse Ground,Wrexham |
| Gibson 50' Ferguson 68' | Report | Deane 42' | Attendance: 11,755 Referee:Stephen Lodge |
| 10 January 2000 | Liverpool (1) | 0 – 1 | Blackburn Rovers (2) | Anfield,Liverpool |
| Report | Blake 84' | Attendance: 32,839 Referee:Graham Poll |
| 11 January 2000 | Gillingham (3) | 3 – 1 | Bradford City (1) | Priestfield Stadium,Gillingham |
| Thomson 39' Ashby 54'Hodge 78' | Report | Saunders 77' | Attendance: 7,091 Referee:Dermot Gallagher |
| 8 January 2000 | Aston Villa (1) | 1 – 0 | Southampton (1) | Villa Park,Birmingham |
| Southgate 20' | Report | Attendance: 25,025 Referee:Neale Barry |
| 8 January 2000 | Sheffield Wednesday (1) | 1 – 1 | Wolverhampton Wanderers (2) | Hillsborough,Sheffield |
| Alexandersson 9' | Report | Sedgley 68' | Attendance: 18,506 Referee:Graham Barber |
| 18 January 2000Replay | Wolverhampton Wanderers (2) | 0 – 0 (a.e.t.) (3-4p) | Sheffield Wednesday (1) | Hillsborough,Sheffield |
| Report | Attendance: 25,201 Referee:Graham Barber | |||
| Penalties | ||||
| 8 January 2000 | Grimsby Town (2) | 0 – 2 | Bolton Wanderers (2) | Blundell Park,Grimsby |
| Guðjohnsen 33' Hansen 54' | Attendance: 4,270 Referee: K M Lynch |
| 8 January 2000 | Everton (1) | 2 – 0 | Birmingham City (2) | Goodison Park,Liverpool |
| Unsworth 75' (pen.),90' (pen.) | Report | Attendance: 25,405 Referee:David Elleray |
| 8 January 2000 | Wrexham (3) | 1 – 2 | Cambridge United (3) | Racecourse Ground,Wrexham |
| Connolly 44' | Benjamin 15' Butler 52' | Attendance: 7,186 Referee:Ray Olivier |
| 8 January 2000 | Tranmere Rovers (2) | 1 – 0 | Sunderland (1) | Prenton Park,Birkenhead |
| Allison 25' Hill 90' | Report | Attendance: 17,344 Referee:Rob Harris |
| 8 January 2000 | Newcastle United (1) | 4 – 1 | Sheffield United (2) | St James' Park,Newcastle |
| Shearer 5' Dabizas 47'Ferguson 59'Gallacher 69' | Report | Smith 17' | Attendance: 36,220 Referee:Mark Halsey |
| 9 January 2000 | Manchester City (2) | 2 – 5 | Leeds United (1) | Maine Road,Manchester |
| Goater 2' Bishop 11' | Report | Bakke 8' Smith 20'Kewell 41',88'Bowyer 66' | Attendance: 29,240 Referee:Dermot Gallagher |
| 8 January 2000 | Fulham (2) | 3 – 0 | Wimbledon (1) | Craven Cottage,London |
| Collins 22',77' Finnan 25' | Report | Attendance: 16,877 Referee:Jeff Winter |
| 8 January 2000 | Coventry City (1) | 3 – 0 | Burnley (3) | Highfield Road,Coventry |
| Chippo 11',69' Whelan 75' | Report | Attendance: 22,774 Referee:Stephen Lodge |
| 8 January 2000 | Plymouth Argyle (4) | 0 – 3 | Preston North End (3) | Home Park,Plymouth |
| O'Sullivan 39' (o.g.) Alexander 60' (pen.)Beswetherick 77' (o.g.) | Attendance: 10,824 Referee:Paul Durkin |
| 19 January 2000 | Chelsea (1) | 2 – 0 | Nottingham Forest (2) | Stamford Bridge,London |
| Leboeuf 57' Wise 86' | Report | Attendance: 30,125 Referee:David Elleray |
| 8 January 2000 | Charlton Athletic (2) | 1 - 0 | Queens Park Rangers (2) | The Valley,London |
| MacDonald 68' | Plummer 67' | Attendance: 16,798 Referee:Rob Styles |
| 9 January 2000 | Arsenal (1) | 0 – 0 | Leicester City (1) | Highbury,London |
| Report | Eadie 81' | Attendance: 35,710 Referee:Mike Riley |
| 19 January 2000Replay | Leicester City (1) | 0 – 0 (a.e.t.) (6–5p) | Arsenal (1) | Filbert Street,Leicester |
| Report | Attendance: 15,235 Referee:Mike Riley | |||
| Penalties | ||||
Gunnlaugsson Savage Fenton Elliott Oakes  Campbell Heskey | ŠukerDixonHughesParlourHenryVieiraGrimandi | |||
| 29 January 2000 | Gillingham (3) | 3 – 1 | Sheffield Wednesday (1) | Priestfield Stadium,Gillingham |
| Saunders 70' Thomson 72'Southall 82' | Report | Sibon 27' | Attendance: 10,130 Referee: M D Reed |
| 31 January 2000 | Blackburn Rovers (2) | 1 – 2 | Newcastle United (1) | Ewood Park,Blackburn |
| Jansen 25' | Report | Shearer 21',79' | Attendance: 29,946 Referee:Paul Durkin |
| 30 January 2000 | Aston Villa (1) | 3 – 2 | Leeds United (1) | Villa Park,Birmingham |
| Carbone 32',58',69' | Report | Harte 13' Bakke 38' | Attendance: 30,026 Referee:Graham Barber |
| 29 January 2000 | Everton (1) | 2 – 0 | Preston North End (3) | Goodison Park,Liverpool |
| Unsworth 64' Moore 90' | Report | Attendance: 37,486 Referee:Mike Riley |
| 29 January 2000 | Fulham (2) | 1 – 2 | Tranmere Rovers (2) | Craven Cottage,London |
| Coleman 18' | Report | Allison 9' Kelly 70' | Attendance: 13,859 Referee:David Elleray |
| 29 January 2000 | Coventry City (1) | 2 – 3 | Charlton Athletic (2) | Highfield Road,Coventry |
| Roussel 15',21' | Report | Robinson 40' Newton 45'Hunt 88' | Attendance: 23,400 Referee:Dermot Gallagher |
| 30 January 2000 | Chelsea (1) | 2 – 1 | Leicester City (1) | Stamford Bridge,London |
| Poyet 35' Weah 48' | Report | Elliott 90' | Attendance: 30,141 Referee:Graham Poll |
| 29 January 2000 | Cambridge United (3) | 1 – 3 | Bolton Wanderers (2) | Abbey Stadium,Cambridge |
| Benjamin 29' | Report | Taylor 53',75' Guðjohnsen 86' | Attendance: 7,523 Referee: M J Brandwood |
| Bolton Wanderers (2) | 1 – 0 | Charlton Athletic (2) |
|---|---|---|
| Guðjohnsen 47' | Report |
| Tranmere Rovers (2) | 2 – 3 | Newcastle United (1) |
|---|---|---|
| Allison 45' Jones 76' | Report | Speed 27' Domi 36'Ferguson 58' |
Aston Villa booked their first FA Cup final appearance since 1957 by beating Bolton Wanderers on penalties after a goalless draw, while Chelsea reached their second final in four years with a narrow 2–1 win over Newcastle United (who had been finalists in the previous two seasons).
| Aston Villa (1) | 0 – 0 | Bolton Wanderers (2) |
|---|---|---|
| Report |
| Chelsea (1) | 2 – 1 | Newcastle United (1) |
|---|---|---|
| Poyet 17',72' | Report | Lee 66' |
The 2000 FA Cup final was contested between Chelsea and Aston Villa at Wembley Stadium, with Chelsea coming out 1-0 winners.Roberto Di Matteo scored the winning goal 17 minutes from the end, three years after he had opened the scoring within the first minute of Chelsea's last FA Cup final win. This was Villa's first FA Cup final for 43 years.
| Chelsea | 1 – 0 | Aston Villa |
|---|---|---|
| Di Matteo 73' | (Report) |
         Chelsea |    Aston Villa |
In the United Kingdom,ITV were the free to air broadcasters for the third consecutive season whileSky Sports were the subscription broadcasters for the twelfth consecutive season.[citation needed]
The matches shown live onITV Sport were:
The matches shown live onSky Sports were: