| Tournament details | |
|---|---|
| Country |  England  Wales | 
| Final positions | |
| Champions | Chelsea (3rd title) | 
| Runner-up | Aston Villa | 
| Tournament statistics | |
| Top goal scorer(s) | Gustavo Poyet (6 goals) | 
The 1999–2000 FA Cup (known as The FA Cup sponsored by AXA for sponsorship reasons) was the 119th staging of the FA Cup. Both the semifinals and final of the competition were played at Wembley Stadium for the last time before reconstruction work began. The competition culminated with the final between Chelsea and Aston Villa. The game was won by a goal from Chelsea's Roberto Di Matteo, giving them a 1–0 victory.
The title holders Manchester United, withdrew from the 1999–2000 competition due to their participation in the 2000 FIFA Club World Championship in South 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 of the Football Association (FA), 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.
Calendar
| 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 winners the previous season, did not enter.
First round proper
This round is the first in which teams from the second Division and Third Division compete with non-League teams.
- Ties were played over the weekend of 30 and 31 October 1999.
- Replays were played on 8, 9 and 10 November 1999.
| 30 October 1999 | Aldershot Town | 1 – 1 | Hednesford Town | Recreation Ground, Aldershot | 
| Abbott  56' Bentley  74'  Bassey  83' | Robinson  51' | Attendance: 3,269 Referee: G Hegley | 
| 8 November 1999 Replay | Hednesford Town | 1 – 2 | Aldershot Town | Keys Park, Hednesford | 
| Lake  44' | Chewins  68' Abbott  87' | Attendance: G Hegley Referee: 1,719 | 
| 31 October 1999 | Barnet | 0 – 1 | Burnley | Underhill Stadium, Barnet | 
| Cook  74' | Attendance: 2,563 Referee: Rob Styles | 
| 31 October 1999 | Bath City | 0 – 2 | Hendon | Twerton Park, Bath | 
| Gentle  74' Genchev  90' | Attendance: 1,690 Referee: S Castle | 
| 30 October 1999 | Blackpool | 2 – 0 | Stoke City | Bloomfield Road, Blackpool | 
| Carlisle  5' Nowland  90' | Attendance: 4,721 Referee: D Laws | 
| 30 October 1999 | Brentford | 2 – 2 | Plymouth Argyle | Griffin Park, London | 
| Owusu  56' Marshall  63' | Stonebridge  43' McGregor  83' | Attendance: 4,287 Referee: Anthony Bates | 
| 9 November 1999 replay | Plymouth Argyle | 2 – 1 (a.e.t.) | Brentford | Home Park, Plymouth | 
| McGregor  67', 112' | Quinn  82' | Attendance: 5,409 Referee: Anthony Bates | 
| 30 October 1999 | Bristol City | 3 – 2 | Mansfield Town | 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 | 0 – 1 | Preston North End | Memorial Stadium, Bristol | 
| McKenna  52' | Attendance: 6,145 Referee: M J Brandwood | 
| 30 October 1999 | Burton Albion | 0 – 0 | Rochdale | Eton Park, Burton upon Trent | 
| Attendance: 3,103 Referee: Mark Halsey | 
| 9 November 1999 Replay | Rochdale | 3 – 0 | Burton Albion | Spotland, Rochdale | 
| Platt  5' Peake  48' Dowe  82' | Attendance: 2,633 Referee: Mark Halsey | 
| 30 October 1999 | Cambridge City | 0 – 2 | Wigan Athletic | City Ground, Cambridge | 
| Barlow  30', 44' | Attendance: 4,024 Referee: Steve Tomlin | 
| 30 October 1999 | Cambridge United | 1 – 0 | Gateshead | Abbey Stadium, Cambridge | 
| Taylor  79' | Fletcher  79'  | Attendance: 2,970 Referee: Peter Walton | 
| 30 October 1999 | Cheltenham Town | 1 – 1 | Gillingham | Whaddon Road, Cheltenham | 
| Brough  77' | Southall  37' | Attendance: 3,188 Referee: Trevor Parkes | 
| 9 November 1999 Replay | Gillingham | 3 – 2 | Cheltenham Town | Priestfield Stadium, Gillingham | 
| Thomson  24' Pennock  41' McGlinchey  77' | Milton  56' Howarth  70' | Attendance: 4,352 | 
| 30 October 1999 | Chesterfield | 1 – 2 | Enfield | Saltergate, Chesterfield | 
| Lomas  49' | Bunn  23' Brown  67' | Attendance: 2,506 Referee: Mark Warren | 
| 30 October 1999 | Darlington | 2 – 1 | Southport | Feethams, Darlington | 
| Tutill  35' Gabbiadini  77' (pen) | Bolland  52' | Attendance: 4,313 Referee: S J Baines | 
| 30 October 1999 | Doncaster Rovers | 0 – 2 | Halifax Town | Belle Vue, Doncaster | 
| Tate  51' Paterson  82' | Attendance: 5,588 Referee: Graham Barber | 
| 30 October 1999 | Exeter City | 2 – 1 | Eastwood Town | 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 | 6 – 0 | Guiseley | 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 | 1 – 0 | Millwall | Victoria Park, Hartlepool | 
| Jones  90' | Attendance: 2,847 Referee: J A Kirkby | 
| 30 October 1999 | Hayes | 2 – 1 | Runcorn | Church Road, Hayes | 
| Bunce  25' Charles  90' | McDonald  45' | Attendance: 890 Referee: Phil Dowd | 
| 30 October 1999 | Hereford United | 1 – 0 | York City | Edgar Street, Hereford | 
| May  77' | Attendance: 2,787 Referee: M Cowburn | 
| 30 October 1999 | Ilkeston Town | 2 – 1 | Carlisle United | New Manor Ground, Ilkeston | 
| Moore  39' Raynor  62' | Harries  18' | Attendance: 1,748 Referee: Mike Dean | 
| 30 October 1999 | Leyton Orient | 1 – 1 | Cardiff City | Brisbane Road, Leyton | 
| Ampadu  56' Joseph  85' | Nugent  39' (pen.) | Attendance: 3,109 Referee: G Cain | 
| 9 November 1999 Replay | Cardiff City | 3 – 1 | Leyton Orient | Ninian Park, Cardiff | 
| Brazier  22' Perrett  51' Nugent  54' | Smith  2' | Attendance: 3,095 Referee: G Cain | 
| 30 October 1999 | Lincoln City | 1 – 0 | Welling United | Sincil Bank, Lincoln | 
| Smith  30' | Attendance: 2,766 Referee: Richard Beeby | 
| 30 October 1999 | Luton Town | 4 – 2 | Kingstonian | 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 | 0 – 0 | Hull City | Moss Rose, Macclesfield | 
| Attendance: 2,401 Referee: P R Richards | 
| 9 November 1999 Replay | Hull City | 4 – 0 | Macclesfield Town | Boothferry Park, Hull | 
| Eyre  3', 61' Greaves  7' Brown  29' | Attendance: 4,844 Referee: P R Richards | 
| 2 November 1999 | Merthyr Tydfil | 2 – 2 | Stalybridge Celtic | Penydarren Park, Merthyr Tydfil | 
| Mitchell  50', 84' | Parr  9' Sullivan  42' | Attendance: 871 | 
| 9 November 1999 Replay | Stalybridge Celtic | 3 – 1 | Merthyr Tydfil | Bower Fold, Stalybridge | 
| Bauress  2' (pen.) Pickford  24' Sullivan  86' | Lima  3' | Attendance: 1,399 | 
| 30 October 1999 | Notts County | 1 – 1 | AFC Bournemouth | Meadow Lane, Nottingham | 
| Rapley  17' | Warren  53' | Attendance: 3,674 Referee: Jeff Winter | 
| 9 November 1999 Replay | AFC Bournemouth | 4 – 2 | Notts County | 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 | 4 – 0 | Chelmsford City | Boundary Park, Oldham | 
| Dudley  28' Sheridan  29' Duxbury  70' Whitehall  83' | Attendance: 4,392 Referee: A N Butler | 
| 30 October 1999 | Oxford United | 3 – 2 | Morecambe | 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 | 1 – 1 | Brighton & Hove Albion | London Road, Peterborough | 
| Clarke  24' | Freeman  35' | Attendance: 7,260 Referee: Neale Barry | 
| 9 November 1999 Replay | Brighton & Hove Albion | 3 – 0 | Peterborough United | Withdean Stadium, Brighton | 
| Rogers  9' Watson  63' Mayo  88' | Attendance: 5,612 Referee: Neale Barry | 
| 30 October 1999 | Reading | 4 – 2 | Yeovil Town | 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 | 3 – 0 | Worthing | Millmoor, Rotherham | 
| Thompson  31' Garner  81' Martindale  90' (pen.) | Attendance: 3,716 Referee: K Hill | 
| 29 October 1999 | Rushden & Diamonds | 2 – 0 | Scunthorpe United | Nene Park, Irthlingborough | 
| Warburton  48' Hamsher  76' (pen.) | Attendance: 4,112 Referee: G Stretton | 
| 30 October 1999 | Shrewsbury Town | 2 – 1 | Northampton Town | Gay Meadow, Shrewsbury | 
| Kerrigan  24' Wilding  70' | Hendon  43' | Attendance: 2,584 Referee: M Fletcher | 
| 30 October 1999 | St Albans City | 0 – 2 | Bamber Bridge | 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 | 2 – 1 | Colchester United | Clarence Park, Swansea | 
| Cusack  83' Watkin  89' | LuaLua  52' | Attendance: 3,622 Referee: R D Furnandiz | 
| 30 October 1999 | Tamworth | 2 – 2 | Bury | The Lamb Ground, Tamworth | 
| Haughton  8' Hallam  75' | Bullock  1' Littlejohn  68' | Attendance: 2,743 Referee: Alan Kaye | 
| 9 November 1999 Replay | Bury | 2 – 1 (a.e.t.) | Tamworth | Gigg Lane, Bury | 
| Billy  86' James  95' | Haughton  15' | Attendance: 2,531 Referee: Alan Kaye | 
| 30 October 1999 | Torquay United | 1 – 0 | Southend United | Plainmoor, Torquay | 
| O'Brien  75' | Attendance: 2,520 Referee: L Cable | 
| 30 October 1999 | Whyteleafe | 0 – 0 | Chester City | Church Road, Whyteleafe | 
| Attendance: 2,164 Referee: P Taylor | 
| 9 November 1999 Replay | Chester City | 3 – 1 | Whyteleafe | Saunders Honda Stadium, Chester | 
| Cross  25', 52' Beckett  48' | Lunn  8' Thornton  45' | Attendance: 2,183 Referee: P Taylor | 
| 30 October 1999 | Wrexham | 1 – 1 | Kettering Town | Racecourse Ground, Wrexham | 
| Roberts  85' | Brown  48' | Attendance: 2,701 Referee: Alan Wiley | 
| 10 November 1999 | Kettering Town | 0 – 2 | Wrexham | Nene Park, Irthlingborough | 
| Roberts  11' Williams  22' | Attendance: 2,611 Referee: Alan Wiley | 
| 30 October 1999 | Wycombe Wanderers | 1 – 1 | Oxford City | Adams Park, High Wycombe | 
| Simpson  67' | Pierson  87' | Attendance: 2,963 Referee: P S Danson | 
| 16 November 1999 | Oxford City | 0 – 1‡ | Wycombe Wanderers | 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]
Second round proper
- Ties were played over the weekend of 20 and 21 November 1999.
- Replays were played on 30 November 1999.
| 20 November 1999 | Blackpool | 2 – 0 | Hendon | Bloomfield Road, Blackpool | 
| Clarkson  69' Durnin  73' | Attendance: 2,975 Referee: K A Leach | 
| 20 November 1999 | AFC Bournemouth | 0 – 2 | Bristol City | Dean Court, Bournemouth | 
| Fletcher  71'  | Murray  21', 53' | Attendance: 5,223 Referee: Bill Jordan | 
| 20 November 1999 | Burnley | 2 – 0 | Rotherham United | Turf Moor, Burnley | 
| Cook  67' Mullin  75' | Attendance: 8,110 Referee: G Laws | 
| 20 November 1999 | Bury | 0 – 0 | Cardiff City | Gigg Lane, Bury | 
| Attendance: 2,603 Referee: Matt Messias | 
| 30 November 1999 Replay | Cardiff City | 1 – 0 (a.e.t.) | Bury | Ninian Park, Cardiff | 
| Ford  120' | Attendance: 4,511 Referee: Matt Messias | 
| 20 November 1999 | Cambridge United | 1 – 0 | Bamber Bridge | Abbey Stadium, Cambridge | 
| Butler  71' (pen.) | Attendance: 3,303 Referee: W C Burns | 
| 20 November 1999 | Exeter City | 2 – 0 | Aldershot Town | St James Park, Exeter | 
| Alexander  32' Flack  35' Power  64'  | Attendance: 4,151 Referee: C R Wilkes | 
| 21 November 1999 | Forest Green Rovers | 0 – 3 | Torquay United | The Lawn Ground, Nailsworth | 
| Brandon  77' Hill  81' Donaldson  87' | Attendance: 2,962 Referee: Phil Joslin | 
| 20 November 1999 | Gillingham | 3 – 1 | Darlington† | Priestfield Stadium, Gillingham | 
| Butters  17' Taylor  43', 47' | Duffield  55' | Attendance: 5,168 Referee: P Jones | 
| 20 November 1999 | Hayes | 2 – 2 | Hull City | Church Road, Hayes | 
| Charles  21', 63' (pen.) | Roddis  55' (o.g.) Edwards  56' Brabin | Attendance: 2,749 Referee: Steve Tomlin | 
| 30 November 1999 Replay | Hull City | 3 – 2 (a.e.t.) | Hayes | Boothferry Park, Hull | 
| Brown  49' Edwards  97' Wood  112' | Gallen  78' Charles  114' | Attendance: 7,000 Referee: Steve Tomlin | 
| 21 November 1999 | Hereford United | 1 – 0 | Hartlepool United | Edgar Street, Hereford | 
| Elmes  54' | Attendance: 4,914 Referee: Anthony Leake | 
| 20 November 1999 | Ilkeston Town | 1 – 1 | Rushden & Diamonds | New Manor Ground, Ilkeston | 
| Eshelby  18' | de Souza  51' | Attendance: 2,737 Referee: A R Hall | 
| 30 November 1999 Replay | Rushden & Diamonds | 3 – 0 | Ilkeston Town | Nene Park, Irthlingborough | 
| Wooding  2' Town  17' Collins  86' | Knapper  74' | Attendance: 4,226 Referee: A R Hall | 
| 19 November 1999 | Luton Town | 2 – 2 | Lincoln City | Kenilworth Road, Luton | 
| Doherty  63', 84' | Gordon  14' Barnett  81' | Attendance: 4,291 Referee: Stephen Lodge | 
| 30 November 1999 Replay | Lincoln City | 0 – 1 | Luton Town | Sincil Bank, Lincoln | 
| Douglas  85' | Attendance: 3,822 Referee: Stephen Lodge | 
| 20 November 1999 | Oldham Athletic | 1 – 0 | Swansea City | Boundary Park, Oldham | 
| Whitehall  45' | Attendance: 4,332 Referee: M Fletcher | 
| 20 November 1999 | Plymouth Argyle | 0 – 0 | Brighton & Hove Albion | Home Park, Plymouth | 
| Freeman  61' Cullip  76'  | Attendance: 7,414 Referee: Rob Harris | 
| 30 November 1999 Replay | Brighton & Hove Albion | 1 – 2 | Plymouth Argyle | Withdean Stadium, Brighton | 
| Cullip  63' | Bastow  9' Hargreaves  65' | Attendance: 5,710 Referee: Stephen Lodge | 
| 20 November 1999 | Preston North End | 0 – 0 | Enfield | Deepdale, Preston | 
| Attendance: 11,566 Referee: P Rejer | 
| 30 November 1999 Replay | Enfield | 0 – 3 | Preston North End F.C. | Clarence Park, St Albans | 
| Protheroe  60' | Eyres  52' Alexander  60' (pen.) Gunnlaugsson  83' | Attendance: 1,808 Referee: P Rejer | 
| 20 November 1999 | Reading | 1 – 1 | Halifax Town | Madejski Stadium, Reading | 
| Caskey  75' (pen.) Parkinson  39'  | Mitchell  60' | Attendance: 5,918 Referee: Richard Beeby | 
| 30 November 1999 Replay | Halifax Town | 0 – 1 | Reading | The Shay, Halifax | 
| Caskey  74' (pen.) Polston  90' | Attendance: 2,156 Referee: Richard Beeby | 
| 20 November 1999 | Shrewsbury Town | 2 – 2 | Oxford United | Gay Meadow, Shrewsbury | 
| Kerrigan  8', 54' | Murphy  63' Folland  77' | Attendance: 3,357 Referee: T Jones | 
| 30 November 1999 Replay | Oxford United | 2 – 1 (a.e.t.) | Shrewsbury Town | Manor Ground, Oxford | 
| Murphy  90', 117' | Jagielka  27' | Attendance: 4,096 Referee: T Jones | 
| 20 November 1999 | Stalybridge Celtic | 1 – 2 | Chester City | Bower Fold, Stalybridge | 
| Scott  8' Parr  90'  | Cross  45' Beckett  69' | Attendance: 3,312 Referee: Michael Ryan | 
| 20 November 1999 | Wrexham | 2 – 1 | Rochdale | Racecourse Ground, Wrexham | 
| Roberts  5' Faulconbridge  88' | Atkinson  33' | Attendance: 3,408 Referee: Trevor Parkes | 
| 20 November 1999 | Wycombe Wanderers | 2 – 2 | Wigan Athletic | Adams Park, High Wycombe | 
| Devine  20' Ryan  90' | Haworth  45', 61' | Attendance: 2,992 Referee: R Olivier | 
| 30 November 1999 Replay | Wigan Athletic | 2 – 1 | Wycombe Wanderers | JJB Stadium, Wigan | 
| Liddell  28' Haworth  80' | Baird  23' | Attendance: 3,967 Referee: R Olivier | 
^† = Darlington advanced as lucky losers
Third round proper
This round marked the first time First Division and Premier League (top-flight) teams played.
- Matches were played on the weekend of 11 and 12 December 1999.
- Replays were played on 21 and 22 December 1999.
| 13 December 1999 | Arsenal | 3 – 1 | Blackpool | Highbury, London | 
| Grimandi  23' Adams  65' Overmars  89' | Clarkson  38' | Attendance: 34,143 Referee: Uriah Rennie | 
| 11 December 1999 | Aston Villa | 2 – 1 | Darlington | Villa Park, Birmingham | 
| Carbone  43' Dublin  63' | Heckingbottom  71' | Attendance: 22,101 Referee: P R Richards | 
| 21 December 1999 | Bolton Wanderers | 1 – 0 | Cardiff City | Reebok Stadium, Bolton | 
| Guðjohnsen  29' | Attendance: 5,734 Referee: G Laws | 
| 10 December 1999 | Cambridge United | 2 – 0 | Crystal Palace | Abbey Stadium, Cambridge | 
| Benjamin  74' Wanless  81' | Mullins  84'  | Attendance: 5,631 Referee: P Taylor | 
| 11 December 1999 | Charlton Athletic | 2 – 1 | Swindon Town | The Valley, London | 
| Kinsella  48', 61' | Gooden  64' | Attendance: 10,939 Referee: A N Butler | 
| 12 December 1999 | Chester City | 1 – 4 | Manchester City | 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 | 1 – 2 | Bradford City | Alexandra Stadium, Crewe | 
| Little  75' | Blake  53' Saunders  83' | Attendance: 6,571 Referee: Alan Wilkie | 
| 11 December 1999 | Derby County | 0 – 1 | Burnley | Pride Park, Derby | 
| Cooke  62' | Attendance: 23,400 Referee: Mike Riley | 
| 11 December 1999 | Exeter City | 0 – 0 | Everton | St James Park, Exeter | 
| Attendance: 6,045 Referee: Steve Bennett | 
| 21 December 1999 Replay | Everton | 1 – 0 | Exeter City | Goodison Park, Liverpool | 
| Barmby  85' | Attendance: 16,869 Referee: Steve Bennett | 
| 11 December 1999 | Fulham | 2 – 2 | Luton Town | Craven Cottage, London | 
| Horsfield  11' Davis  14' | George  6' Spring  82' | Attendance: 8,251 Referee: G B Frankland | 
| 21 December 1999 Replay | Luton Town | 0 – 3 | Fulham | Kenilworth Road, Luton | 
| Hayles  57', 60' Hayward  63' | Attendance: 8,170 Referee: G B Frankland | 
| 11 December 1999 | Grimsby Town | 3 – 2 | Stockport County | Blundell Park, Cleethorpes | 
| Livingstone  57', 60' Bradley Allen  63' | Attendance: 3,400 | 
| 11 December 1999 | Hereford United | 0 – 0 | Leicester City | Edgar Street, Hereford | 
| Attendance: 7,795 Referee: Mike Dean | 
| 22 December 1999 Replay | Leicester City | 2 – 1 (a.e.t.) | Hereford United | Filbert Street, Leicester | 
| Elliott  78' Izzet  104' | Fewings  40' | Attendance: 12,157 Referee: Mike Dean | 
| 12 December 1999 | Huddersfield Town | 0 – 2 | Liverpool | Alfred McAlpine Stadium, Huddersfield | 
| Report | Camara  36' Matteo  59' | Attendance: 23,678 Referee: Rob Harris | 
| 11 December 1999 | Hull City | 1 – 6 | Chelsea | 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 | 0 – 1 | Southampton | Portman Road, Ipswich | 
| Richards  40' | Attendance: 14,383 Referee: Graham Barber | 
| 12 December 1999 | Leeds United | 2 – 0 | Port Vale | Elland Road, Leeds | 
| Bakke  61', 68' | Attendance: 11,912 Referee: Steve Dunn | 
| 11 December 1999 | Norwich City | 1 – 3 | Coventry City | Carrow Road, Norwich | 
| Llewellyn  66' | Whelan  58' Roussel  76' Eustace  84' | Attendance: 15,702 Referee: Paul Alcock | 
| 10 December 1999 | Nottingham Forest | 1 – 1 | Oxford United | City Ground, Nottingham | 
| Llewellyn  66' | Whelan  58' | Attendance: 8,079 Referee: Andy D'Urso | 
| 8 January 2000 Replay | Oxford United | 1 – 3 | Nottingham Forest | 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 | 2 – 1 | Oldham Athletic | Deepdale, Preston | 
| Macken  6' Alexander  69' (pen.) | Adams  85' Hotte  69' | Attendance: 9,940 Referee: Paul Danson | 
| 11 December 1999 | Queens Park Rangers | 1 – 1 | Torquay United | Loftus Road, London | 
| Wardley  9' | O'Brien  82' | Attendance: 8,843 Referee: K A Leach | 
| 21 December 1999 Replay | Torquay United | 2 – 3 | Queens Park Rangers | Plainmoor, Torquay | 
| Bedeau  52' Thomas  80' | Wardley  56', 74' Kiwomya  71' | Attendance: 5,232 Referee: K A Leach | 
| 11 December 1999 | Reading | 1 – 1 | Plymouth Argyle | Madejski Stadium, Reading | 
| McIntyre  37' | Hargreaves  82' | Attendance: 8,536 Referee: Alan Wiley | 
| 21 December 1999 Replay | Plymouth Argyle | 1 – 0 | Reading | Home Park, Plymouth | 
| Heathcote  88' | Smith  39'  | Attendance: 8,965 Referee: Alan Wiley | 
| 12 December 1999 | Sheffield United | 1 – 1 | Rushden & Diamonds | Bramall Lane, Sheffield | 
| Bent  14' | Brady  45' | Attendance: 10,104 Referee: B Knight | 
| 21 December 1999 Replay | Rushden & Diamonds | 1 – 1 (a.e.t.) (5-6 p) | Sheffield United | Nene Park, Irthlingborough | 
| Warburton  105' | Derry  103' | Attendance: 6,010 Referee: B Knight | 
| 11 December 1999 | Sheffield Wednesday | 1 – 0 | Bristol City | Hillsborough, Sheffield | 
| Booth  24' Quinn  90' | Attendance: 11,644 Referee: M Reed | 
| 11 December 1999 | Sunderland | 1 – 0 | Portsmouth | Stadium of Light, Sunderland | 
| McCann  24' | Panopoulos  40'  | Attendance: 26,535 Referee: Neale Barry | 
| 12 December 1999 | Tottenham Hotspur | 1 – 1 | Newcastle United | White Hart Lane, London | 
| Iversen  57' | Speed  77' | Attendance: 33,116 Referee: Graham Poll | 
| 22 December 1999 Replay | Newcastle United | 6 – 1 | Tottenham Hotspur | 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 | 1 – 0 | West Ham United | Prenton Park, Birkenhead | 
| Henry  21' | Attendance: 13,629 Referee: Dermot Gallagher | 
| 11 December 1999 | Walsall | 1 – 1 | Gillingham | Bescot Stadium, Walsall | 
| Robins  75' (pen.) | Southall  27' | Attendance: 4,314 Referee: Eddie Wolstenholme | 
| 8 January 2000 Replay | Gillingham | 2 – 1 (a.e.t.) | Walsall | Priestfield Stadium, Gillingham | 
| Barras  38' (og) Thomson  100' | Lárusson  44' | Attendance: 6,538 Referee: Eddie Wolstenholme | 
| 11 December 1999 | Watford | 0 – 1 | Birmingham City | Vicarage Road, Watford | 
| Rowett  66' | Attendance: 8,144 Referee: Paul Durkin | 
| 11 December 1999 | West Bromwich Albion | 2 – 2 | Blackburn Rovers | The Hawthorns, West Bromwich | 
| Hughes  66' Evans  80' | Frandsen  65' Blake  70' | Attendance: 10,609 Referee: Rob Styles | 
| 22 December 1999 Replay | Blackburn Rovers | 2 – 0 (a.e.t.) | West Bromwich Albion | Ewood Park, Blackburn | 
| Duff  94' Carsley  114' (pen.) | Attendance: 11,766 Referee: Rob Styles | 
| 11 December 1999 | Wigan Athletic | 0 – 1 | Wolverhampton Wanderers | JJB Stadium, Wigan | 
| Robinson  90' | Attendance: 10,531 Referee: C Wilkes | 
| 11 December 1999 | Wimbledon | 1 – 0 | Barnsley | Selhurst Park, London | 
| Cort  34' | Attendance: 4,505 Referee: Mark Halsey | 
| 11 December 1999 | Wrexham | 2 – 1 | Middlesbrough | Racecourse Ground, Wrexham | 
| Gibson  50' Ferguson  68' | Report | Deane  42' | Attendance: 11,755 Referee: Stephen Lodge | 
Fourth round proper
- Ties played on weekend of 8 and 9 January 2000.
- Replays played on 18 and 19 January 2000.
| 10 January 2000 | Liverpool | 0 – 1 | Blackburn Rovers | Anfield, Liverpool | 
| Report | Blake  84' | Attendance: 32,839 Referee: Graham Poll | 
| 11 January 2000 | Gillingham | 3 – 1 | Bradford City | Priestfield Stadium, Gillingham | 
| Thomson  39' Ashby  54' Hodge  78' | Report | Saunders  77' | Attendance: 7,091 Referee: Dermot Gallagher | 
| 8 January 2000 | Aston Villa | 1 – 0 | Southampton | Villa Park, Birmingham | 
| Southgate  20' | Report | Attendance: 25,025 Referee: Neale Barry | 
| 8 January 2000 | Sheffield Wednesday | 1 – 1 | Wolverhampton Wanderers | Hillsborough, Sheffield | 
| Alexandersson  9' | Report | Sedgley  68' | Attendance: 18,506 Referee: Graham Barber | 
| 18 January 2000 Replay | Wolverhampton Wanderers | 0 – 0 (a.e.t.) (3-4 p) | Sheffield Wednesday | Hillsborough, Sheffield | 
| Report | Attendance: 25,201 Referee: Graham Barber | |||
| Penalties | ||||
| 8 January 2000 | Grimsby Town | 0 – 2 | Bolton Wanderers | Blundell Park, Grimsby | 
| Guðjohnsen  33' Hansen  54' | Attendance: 4,270 Referee: K M Lynch | 
| 8 January 2000 | Everton | 2 – 0 | Birmingham City | Goodison Park, Liverpool | 
| Unsworth  75' (pen.), 90' (pen.) | Report | Attendance: 25,405 Referee: David Elleray | 
| 8 January 2000 | Wrexham | 1 – 2 | Cambridge United | Racecourse Ground, Wrexham | 
| Connolly  44' | Benjamin  15' Butler  52' | Attendance: 7,186 Referee: Ray Olivier | 
| 8 January 2000 | Tranmere Rovers | 1 – 0 | Sunderland | Prenton Park, Birkenhead | 
| Allison  25' Hill  90'  | Report | Attendance: 17,344 Referee: Rob Harris | 
| 8 January 2000 | Newcastle United | 4 – 1 | Sheffield United | 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 – 5 | Leeds United | 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 | 3 – 0 | Wimbledon | Craven Cottage, London | 
| Collins  22', 77' Finnan  25' | Report | Attendance: 16,877 Referee: Jeff Winter | 
| 8 January 2000 | Coventry City | 3 – 0 | Burnley | Highfield Road, Coventry | 
| Chippo  11', 69' Whelan  75' | Report | Attendance: 22,774 Referee: Stephen Lodge | 
| 8 January 2000 | Plymouth Argyle | 0 – 3 | Preston North End | Home Park, Plymouth | 
| O'Sullivan  39' (og) Alexander  60' (pen.) Beswetherick  77' (og) | Attendance: 10,824 Referee: Paul Durkin | 
| 19 January 2000 | Chelsea | 2 – 0 | Nottingham Forest | Stamford Bridge, London | 
| Leboeuf  57' Wise  86' | Report | Attendance: 30,125 Referee: David Elleray | 
| 8 January 2000 | Charlton Athletic | 2 – 0 | Queens Park Rangers | The Valley, London | 
| MacDonald  68' | Plummer  67'  | Attendance: 16,798 Referee: Rob Styles | 
| 9 January 2000 | Arsenal | 0 – 0 | Leicester City | Highbury, London | 
| Report | Eadie  81'  | Attendance: 35,710 Referee: Mike Riley | 
Fifth round proper
- Ties played on weekend of 29 and 30 January 2000.
- The shock result of the round came when Division Two Gillingham (who had yet to play in the top two divisions) defeated Premier League side Sheffield Wednesday 3–1.
| 29 January 2000 | Gillingham | 3 – 1 | Sheffield Wednesday | Priestfield Stadium, Gillingham | 
| Saunders  70' Thomson  72' Southall  82' | Report | Sibon  27' | Attendance: 10,130 Referee: M D Reed | 
| 31 January 2000 | Blackburn Rovers | 1 – 2 | Newcastle United | Ewood Park, Blackburn | 
| Jansen  25' | Report | Shearer  21', 79' | Attendance: 29,946 Referee: Paul Durkin | 
| 30 January 2000 | Aston Villa | 3 – 2 | Leeds United | Villa Park, Birmingham | 
| Carbone  32', 58', 69' | Report | Harte  13' Bakke  38' | Attendance: 30,026 Referee: Graham Barber | 
| 29 January 2000 | Everton | 2 – 0 | Preston North End | Goodison Park, Liverpool | 
| Unsworth  64' Moore  90' | Report | Attendance: 37,486 Referee: Mike Riley | 
| 29 January 2000 | Fulham | 1 – 2 | Tranmere Rovers | Craven Cottage, London | 
| Coleman  18' | Report | Allison  9' Kelly  70' | Attendance: 13,859 Referee: David Elleray | 
| 29 January 2000 | Coventry City | 2 – 3 | Charlton Athletic | Highfield Road, Coventry | 
| Roussel  15', 21' | Report | Robinson  40' Newton  45' Hunt  88' | Attendance: 23,400 Referee: Dermot Gallagher | 
| 30 January 2000 | Chelsea | 2 – 1 | Leicester City | Stamford Bridge, London | 
| Poyet  35' Weah  48' | Report | Elliott  90' | Attendance: 30,141 Referee: Graham Poll | 
| 29 January 2000 | Cambridge United | 1 – 3 | Bolton Wanderers | Abbey Stadium, Cambridge | 
| Benjamin  29' | Report | Taylor  53', 75' Guðjohnsen  86' | Attendance: 7,523 Referee: M J Brandwood | 
Sixth round proper
| Tranmere Rovers | 2 – 3 | Newcastle United | 
|---|---|---|
| Allison  45' Jones  76' | Report | Speed  27' Domi  36' Ferguson  58' | 
Semi-finals
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 first final after just three years with a narrow 2–1 win over Newcastle United (who had been finalists in the previous two seasons).
- Aston Villa win 4–1 on penalties. Steve Stone, Lee Hendrie, Gareth Barry and Dion Dublin all scored for Aston Villa. Dean Holdsworth scored for Bolton.
| Chelsea | 2 – 1 | Newcastle United | 
|---|---|---|
| Poyet  17', 72' | Report | Lee  66' | 
Final
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 | 
Media coverage
In the United Kingdom, ITV were the free to air broadcasters for the third consecutive season while Sky Sports were the subscription broadcasters for the twelfth consecutive season.
The matches shown live on ITV Sport were:
- Huddersfield Town 0-2 Liverpool (R3)
- Arsenal 0-0 Leicester City (R4)
- Aston Villa 3-2 Leeds United (R5)
- Tranmere Rovers 2-3 Newcastle United (QF)
- Bolton Wanderers 0-0 Aston Villa (SF)
- Chelsea 1-0 Aston Villa (Final)
The matches shown live on Sky Sports were: 
- Rushden & Diamonds 2-0 Scunthorpe United (R1)
- Barnet 0-1 Burnley (R1)
- Kettering Town 0-2 Wrexham (R1 Replay)
- Luton Town 2-2 Lincoln City (R2)
- Hereford United 1-0 Hartlepool United (R2)
- Lincoln City 0-1 Luton Town (R2 Replay)
- Tottenham Hotspur 1-1 Newcastle United (R3)
- Ipswich Town 0-1 Southampton (R3)
- Newcastle United 6-1 Tottenham Hotspur (R3 Replay)
- Manchester City 2-5 Leeds United (R4)
- Liverpool 0-1 Blackburn Rovers (R4)
- Leicester City 0-0 Arsenal (R4 Replay)
- Chelsea 2-1 Leicester City (R5)
- Blackburn Rovers 1-2 Newcastle United (R5)
- Everton 1-2 Aston Villa (QF)
- Chelsea 2-1 Newcastle United (SF)
- Chelsea 1-0 Aston Villa (Final)
References
- ↑ United pull out of FA Cup BBC News, 30 June 1999.
- ↑ Club World Cup: David Beckham sent off for Manchester United BBC News, 11 December 2012.
- ↑ FA Cup to have 'wild card' entry BBC News, 8 November 1999.
- ↑ Lucky Darlington land Villa trip BBC News, 11 December 1999.
- ↑ Staniforth, Tommy (10 November 1999). "Fire at Wycombe calls halt to Cup tie". The Independent. London. Archived from the original on 1 May 2022. Retrieved 15 May 2009.
- ↑ Malam, Colin (21 May 2000). "Chelsea 1 Aston Villa 0". The Telegraph. Archived from the original on 24 October 2007. Retrieved 10 May 2012.

