1999-2000 FA Cup
Birinci tur

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| 30 Ekim 1999 | Aldershot Town | 1 - 1 | Hednesford Town | Recreation Ground, Aldershot |
|  | Abbott  56' Bentley  74' Bassey  83' |  | Robinson  51' | Stadyum: Recreation Ground, Aldershot  Seyirci: 3.269 Hakem: G Hegley  |
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| 8 Kasım 1999 | Hednesford Town | 1 - 2 | Aldershot Town | Keys Park, Hednesford |
|  | Lake  44' |  | Chewins  68' Abbott  87' | Stadyum: Keys Park, Hednesford  Seyirci: G Hegley Hakem: 1.719  |
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| 31 Ekim 1999 | Barnet | 0 - 1 | Burnley | Underhill Stadyumu, Barnet |
|  |  |  | Cook  74' | Stadyum: Underhill Stadyumu, Barnet  Seyirci: 2.563 Hakem: Rob Styles  |
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| 31 Ekim 1999 | Bath City | 0 - 2 | Hendon | Twerton Park, Bath |
|  |  |  | Gentle  74' Genchev  90' | Stadyum: Twerton Park, Bath  Seyirci: 1.690 Hakem: S Castle  |
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| 30 Ekim 1999 | Blackpool | 2 - 0 | Stoke City | Bloomfield Road, Blackpool |
|  | Carlisle  5' Nowland  90' |  |  | Stadyum: Bloomfield Road, Blackpool  Seyirci: 4.721 Hakem: D Laws  |
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| 30 Ekim 1999 | Brentford | 2 - 2 | Plymouth Argyle | Griffin Park, Londra |
|  | Owusu  56' Marshall  63' |  | Stonebridge  43' McGregor  83' | Stadyum: Griffin Park, Londra  Seyirci: 4.287 Hakem: Anthony Bates  |
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| 9 Kasım 1999 | Plymouth Argyle | 2 - 1 (uz.) | Brentford | Home Park, Plymouth |
|  | McGregor  67', 112' |  | Quinn  82' | Stadyum: Home Park, Plymouth  Seyirci: 5.409 Hakem: Anthony Bates  |
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| 30 Ekim 1999 | Bristol City | 3 - 2 | Mansfield Town | Ashton Gate, Bristol |
|  | Tinnion  44', 50' Murray  65' Taylor  9' |  | Lormor  10' (pen.) Blake  89' | Stadyum: Ashton Gate, Bristol  Seyirci: 5.411 Hakem: R Olivier  |
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| 30 Ekim 1999 | Bristol Rovers | 0 - 1 | Preston North End | Memorial Stadyumu, Bristol |
|  |  |  | McKenna  52' | Stadyum: Memorial Stadyumu, Bristol  Seyirci: 6.145 Hakem: M J Brandwood  |
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| 30 Ekim 1999 | Burton Albion | 0 - 0 | Rochdale | Eton Park, Burton upon Trent |
|  |  |  |  | Stadyum: Eton Park, Burton upon Trent  Seyirci: 3.103 Hakem: Mark Halsey  |
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| 9 Kasım 1999 | Rochdale | 3 - 0 | Burton Albion | Spotland, Rochdale |
|  | Platt  5' Peake  48' Dowe  82' |  |  | Stadyum: Spotland, Rochdale  Seyirci: 2.633 Hakem: Mark Halsey  |
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| 30 Ekim 1999 | Cambridge City | 0 - 2 | Wigan Athletic | City Ground, Cambridge |
|  |  |  | Barlow  30', 44' | Stadyum: City Ground, Cambridge  Seyirci: 4.024 Hakem: Steve Tomlin  |
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| 30 Ekim 1999 | Cambridge United | 1 - 0 | Gateshead | Abbey Stadyumu, Cambridge |
|  | Taylor  79' |  | Fletcher  79' | Stadyum: Abbey Stadyumu, Cambridge  Seyirci: 2.970 Hakem: Peter Walton  |
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| 30 Ekim 1999 | Cheltenham Town | 1 - 1 | Gillingham | Whaddon Road, Cheltenham |
|  | Brough  77' |  | Southall  37' | Stadyum: Whaddon Road, Cheltenham  Seyirci: 3.188 Hakem: Trevor Parkes  |
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| 9 Kasım 1999 | Gillingham | 3 - 2 | Cheltenham Town | Priestfield Stadyumu, Gillingham |
|  | Thomson  24' Pennock  41' McGlinchey  77' |  | Milton  56' Howarth  70' | Stadyum: Priestfield Stadyumu, Gillingham  Seyirci: 4.352  |
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| 30 Ekim 1999 | Chesterfield | 1 - 2 | Enfield | Saltergate, Chesterfield |
|  | Lomas  49' |  | Bunn  23' Brown  67' | Stadyum: Saltergate, Chesterfield  Seyirci: 2.506 Hakem: Mark Warren  |
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| 30 Ekim 1999 | Darlington | 2 - 1 | Southport | Feethams, Darlington |
|  | Tutill  35' Gabbiadini  77' (pen.) |  | Bolland  52' | Stadyum: Feethams, Darlington  Seyirci: 4.313 Hakem: S J Baines  |
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| 30 Ekim 1999 | Doncaster Rovers | 0 - 2 | Halifax Town | Belle Vue, Doncaster |
|  |  |  | Tate  51' Paterson  82' | Stadyum: Belle Vue, Doncaster  Seyirci: 5.588 Hakem: Graham Barber  |
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| 30 Ekim 1999 | Exeter City | 2 - 1 | Eastwood Town | St James Park, Exeter |
|  | Flack  40' Gale  47' Bradley  65' |  | Smith  56' | Stadyum: St James Park, Exeter  Seyirci: 2.441 Hakem: S W Mathieson  |
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| 30 Ekim 1999 | Forest Green Rovers | 6 - 0 | Guiseley | The Lawn Ground, Nailsworth |
|  | Hunt  1', 31', 62' McGregor  25' Drysdale  38' Sykes  51' |  | Hogarth  66' | Stadyum: The Lawn Ground, Nailsworth  Seyirci: 1.047 Hakem: M J Jones  |
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| 31 Ekim 1999 | Hartlepool United | 1 - 0 | Millwall | Victoria Park, Hartlepool |
|  | Jones  90' |  |  | Stadyum: Victoria Park, Hartlepool  Seyirci: 2.847 Hakem: J A Kirkby  |
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| 30 Ekim 1999 | Hayes | 2 - 1 | Runcorn | Church Road, Hayes |
|  | Bunce  25' Charles  90' |  | McDonald  45' | Stadyum: Church Road, Hayes  Seyirci: 890 Hakem: Phil Dowd  |
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| 30 Ekim 1999 | Hereford United | 1 - 0 | York City | Edgar Street, Hereford |
|  | Mayıs  77' |  |  | Stadyum: Edgar Street, Hereford  Seyirci: 2.787 Hakem: M Cowburn  |
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| 30 Ekim 1999 | Ilkeston Town | 2 - 1 | Carlisle United | New Manor Ground, Ilkeston |
|  | Moore  39' Raynor  62' |  | Harries  18' | Stadyum: New Manor Ground, Ilkeston  Seyirci: 1.748 Hakem: Mike Dean  |
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| 30 Ekim 1999 | Leyton Orient | 1 - 1 | Cardiff City | Brisbane Road, Leyton |
|  | Ampadu  56' Joseph  85' |  | Nugent  39' (pen.) | Stadyum: Brisbane Road, Leyton  Seyirci: 3.109 Hakem: G Cain  |
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| 9 Kasım 1999 | Cardiff City | 3 - 1 | Leyton Orient | Ninian Park, Cardiff |
|  | Brazier  22' Perrett  51' Nugent  54' |  | Smith  2' | Stadyum: Ninian Park, Cardiff  Seyirci: 3.095 Hakem: G Cain  |
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| 30 Ekim 1999 | Lincoln City | 1 - 0 | Welling United | Sincil Bank, Lincoln |
|  | Smith  30' |  |  | Stadyum: Sincil Bank, Lincoln  Seyirci: 2.766 Hakem: Richard Beeby  |
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| 30 Ekim 1999 | Luton Town | 4 - 2 | Kingstonian | Kenilworth Road, Luton |
|  | Gray  11' George  66' Spring  76' Taylor  79' |  | Crossley  35' Leworthy  47' | Stadyum: Kenilworth Road, Luton  Seyirci: 4.682 Hakem: Phil Joslin  |
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| 30 Ekim 1999 | Macclesfield Town | 0 - 0 | Hull City | Moss Rose, Macclesfield |
|  |  |  |  | Stadyum: Moss Rose, Macclesfield  Seyirci: 2.401 Hakem: P R Richards  |
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| 9 Kasım 1999 | Hull City | 4 - 0 | Macclesfield Town | Boothferry Park, Hull |
|  | Eyre  3', 61' Greaves  7' Brown  29' |  |  | Stadyum: Boothferry Park, Hull  Seyirci: 4.844 Hakem: P R Richards  |
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| 2 Kasım 1999 | Merthyr Tydfil | 2 - 2 | Stalybridge Celtic | Penydarren Park, Merthyr Tydfil |
|  | Mitchell  50', 84' |  | Parr  9' Sullivan  42' | Stadyum: Penydarren Park, Merthyr Tydfil  Seyirci: 871  |
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| 9 Kasım 1999 | Stalybridge Celtic | 3 - 1 | Merthyr Tydfil | Bower Fold, Stalybridge |
|  | Bauress  2' (pen.) Pickford  24' Sullivan  86' |  | Lima  3' | Stadyum: Bower Fold, Stalybridge  Seyirci: 1.399  |
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| 30 Ekim 1999 | Notts County | 1 - 1 | Bournemouth | Meadow Lane, Nottingham |
|  | Rapley  17' |  | Warren  53' | Stadyum: Meadow Lane, Nottingham  Seyirci: 3.674 Hakem: Jeff Winter  |
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| 9 Kasım 1999 | Bournemouth | 4 - 2 | Notts County | Dean Court, Bournemouth |
|  | Fletcher  44' (67) Robinson  89' (pen.) Stein  89' |  | Redmile  78' Tierney  84' | Stadyum: Dean Court, Bournemouth  Seyirci: 4.026 Hakem: Jeff Winter  |
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| 30 Ekim 1999 | Oldham Athletic | 4 - 0 | Chelmsford City | Boundary Park, Oldham |
|  | Dudley  28' Sheridan  29' Duxbury  70' Whitehall  83' |  |  | Stadyum: Boundary Park, Oldham  Seyirci: 4.392 Hakem: A N Butler  |
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| 30 Ekim 1999 | Oxford United | 3 - 2 | Morecambe | Manor Ground, Oxford |
|  | Lilley  12' Powell  58' Abbey  87' |  | Wright  28' Jackson  47' | Stadyum: Manor Ground, Oxford  Seyirci: 3.504 Hakem: A R Hall  |
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| 30 Ekim 1999 | Peterborough United | 1 - 1 | Brighton & Hove Albion | London Road, Peterborough |
|  | Clarke  24' |  | Freeman  35' | Stadyum: London Road, Peterborough  Seyirci: 7.260 Hakem: Neale Barry  |
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| 9 Kasım 1999 | Brighton & Hove Albion | 3 - 0 | Peterborough United | Withdean Stadyumu, Brighton |
|  | Rogers  9' Watson  63' Mayo  88' |  |  | Stadyum: Withdean Stadyumu, Brighton  Seyirci: 5.612 Hakem: Neale Barry  |
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| 30 Ekim 1999 | Reading | 4 - 2 | Yeovil Town | Madejski Stadyumu, Reading |
|  | Bernal  31' Caskey  63' (pen.) Hunter  80' Williams  87' |  | Foster  36' Eaton  90' | Stadyum: Madejski Stadyumu, Reading  Seyirci: 8.032 Hakem: Bill Jordan  |
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| 30 Ekim 1999 | Rotherham United | 3 - 0 | Worthing | Millmoor, Rotherham |
|  | Thompson  31' Garner  81' Martindale  90' (pen.) |  |  | Stadyum: Millmoor, Rotherham  Seyirci: 3.716 Hakem: K Hill  |
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| 29 Ekim 1999 | Rushden & Diamonds | 2 - 0 | Scunthorpe United | Nene Park, Irthlingborough |
|  | Warburton  48' Hamsher  76' (pen.) |  |  | Stadyum: Nene Park, Irthlingborough  Seyirci: 4.112 Hakem: G Stretton  |
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| 30 Ekim 1999 | Shrewsbury Town | 2 - 1 | Northampton Town | Gay Meadow, Irthlingborough |
|  | Kerrigan  24' Wilding  70' |  | Hendon  43' | Stadyum: Gay Meadow, Irthlingborough  Seyirci: 2.584 Hakem: M Fletcher  |
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| 30 Ekim 1999 | St Albans City | 0 - 2 | Bamber Bridge | Clarence Park, St Albans |
|  | Randall  90' |  | Whittaker  45' Carroll  89' Jones  59' Maddock  89' | Stadyum: Clarence Park, St Albans  Seyirci: 1.127 Hakem: B Curson  |
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| 30 Ekim 1999 | Swansea City | 2 - 1 | Colchester United | Clarence Park, Swansea |
|  | Cusack  83' Watkin  89' |  | LuaLua  52' | Stadyum: Clarence Park, Swansea  Seyirci: 3.622 Hakem: R D Furnandiz  |
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| 30 Ekim 1999 | Tamworth | 2 - 2 | Bury | The Lamb Ground, Tamworth |
|  | Haughton  8' Hallam  75' |  | Bullock  1' Littlejohn  68' | Stadyum: The Lamb Ground, Tamworth  Seyirci: 2.743 Hakem: Alan Kaye  |
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| 9 Kasım 1999 | Bury | 2 - 1 (uz.) | Tamworth | Gigg Lane, Tamworth |
|  | Billy  86' James  95' |  | Haughton  15' | Stadyum: Gigg Lane, Tamworth  Seyirci: 2.531 Hakem: Alan Kaye  |
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| 30 Ekim 1999 | Torquay United | 1 - 0 | Southend United | Plainmoor, Torquay |
|  | O'Brien  75' |  |  | Stadyum: Plainmoor, Torquay  Seyirci: 2.520 Hakem: L Cable  |
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| 30 Ekim 1999 | Whyteleafe | 0 - 0 | Chester City | Church Road, Whyteleafe |
|  |  |  |  | Stadyum: Church Road, Whyteleafe  Seyirci: 2.164 Hakem: P Taylor  |
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| 9 Kasım 1999 | Chester City | 3 - 1 | Whyteleafe | Saunders Honda Stadyumu, Chester |
|  | Cross  25', 52' Beckett  48' |  | Lunn  8' Thornton  45' | Stadyum: Saunders Honda Stadyumu, Chester  Seyirci: 2.183 Hakem: P Taylor  |
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| 30 Ekim 1999 | Wrexham | 1 - 1 | Kettering Town | Racecourse Ground, Wrexham |
|  | Roberts  85' |  | Brown  48' | Stadyum: Racecourse Ground, Wrexham  Seyirci: 2.701 Hakem: Alan Wiley  |
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| 10 Kasım 1999 | Kettering Town | 0 - 2 | Wrexham | Nene Park, Irthlingborough |
|  |  |  | Roberts  11' Williams  22' | Stadyum: Nene Park, Irthlingborough  Seyirci: 2.611 Hakem: Alan Wiley  |
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| 30 Ekim 1999 | Wycombe Wanderers | 1 - 1 | Oxford City | Adams Park, High Wycombe |
|  | Simpson  67' |  | Pierson  87' | Stadyum: Adams Park, High Wycombe  Seyirci: 2.963 Hakem: P S Danson  |
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| 16 Kasım 1999 | Oxford City | 0 - 1‡ | Wycombe Wanderers | Manor Ground, Oxford |
|  |  |  | Brown  51' | Stadyum: Manor Ground, Oxford  Seyirci: 4.004 Hakem: P S Danson  |