1999-2000 FA Cup
İkinci tur

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| 20 Kasım 1999 | Blackpool | 2 - 0 | Hendon | Bloomfield Road, Blackpool |
|  | Clarkson  69' Durnin  73' |  |  | Stadyum: Bloomfield Road, Blackpool  Seyirci: 2.975 Hakem: K A Leach  |
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| 20 Kasım 1999 | Bournemouth | 0 - 2 | Bristol City | Dean Court, Bournemouth |
|  | Fletcher  71' |  | Murray  21', 53' | Stadyum: Dean Court, Bournemouth  Seyirci: 5.223 Hakem: Bill Jordan  |
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| 20 Kasım 1999 | Burnley | 2 - 0 | Rotherham United | Turf Moor, Burnley |
|  | Cook  67' Mullin  75' |  |  | Stadyum: Turf Moor, Burnley  Seyirci: 8.110 Hakem: G Laws  |
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| 20 Kasım 1999 | Bury | 0 - 0 | Cardiff City | Gigg Lane, Bury |
|  |  |  |  | Stadyum: Gigg Lane, Bury  Seyirci: 2.603 Hakem: Matt Messias  |
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| 30 Kasım 1999 | Cardiff City | 1 - 0 (uz.) | Bury | Ninian Park, Cardiff |
|  | Ford  120' |  |  | Stadyum: Ninian Park, Cardiff  Seyirci: 4.511 Hakem: Matt Messias  |
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| 20 Kasım 1999 | Cambridge United | 1 - 0 | Bamber Bridge | Abbey Stadyumu, Cambridge |
|  | Butler  71' (pen.) |  |  | Stadyum: Abbey Stadyumu, Cambridge  Seyirci: 3.303 Hakem: W C Burns  |
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| 20 Kasım 1999 | Exeter City | 2 - 0 | Aldershot Town | St James Park, Exeter |
|  | Alexander  32' Flack  35' Power  64' |  |  | Stadyum: St James Park, Exeter  Seyirci: 4.151 Hakem: C R Wilkes  |
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| 21 Kasım 1999 | Forest Green Rovers | 0 - 3 | Torquay United | The Lawn Ground, Nailsworth |
|  |  |  | Brandon  77' Hill  81' Donaldson  87' | Stadyum: The Lawn Ground, Nailsworth  Seyirci: 2.962 Hakem: Phil Joslin  |
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| 20 Kasım 1999 | Gillingham | 3 - 1 | Darlington | Priestfield Stadyumu, Gillingham |
|  | Butters  17' Taylor  43', 47' |  | Duffield  55' | Stadyum: Priestfield Stadyumu, Gillingham  Seyirci: 5.168 Hakem: P Jones  |
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| 20 Kasım 1999 | Hayes | 2 - 2 | Hull City | Church Road, Hayes |
|  | Charles  21', 63' (pen.) |  | Roddis  55' (kk) Edwards  56' Brabin  | Stadyum: Church Road, Hayes  Seyirci: 2.749 Hakem: Steve Tomlin  |
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| 30 Kasım 1999 | Hull City | 3 - 2 (uz.) | Hayes | Boothferry Park, Hull |
|  | Brown  49' Edwards  97' Wood  112' |  | Gallen  78' Charles  114' | Stadyum: Boothferry Park, Hull  Seyirci: 7.000 Hakem: Steve Tomlin  |
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| 21 Kasım 1999 | Hereford United | 1 - 0 | Hartlepool United | Edgar Street, Hereford |
|  | Elmes  54' |  |  | Stadyum: Edgar Street, Hereford  Seyirci: 4.914 Hakem: Anthony Leake  |
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| 20 Kasım 1999 | Ilkeston Town | 1 - 1 | Rushden & Diamonds | New Manor Ground, Ilkeston |
|  | Eshelby  18' |  | de Souza  51' | Stadyum: New Manor Ground, Ilkeston  Seyirci: 2.737 Hakem: A R Hall  |
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| 30 Kasım 1999 | Rushden & Diamonds | 3 - 0 | Ilkeston Town | Nene Park, Irthlingborough |
|  | Wooding  2' Town  17' Collins  86' |  | Knapper  74' | Stadyum: Nene Park, Irthlingborough  Seyirci: 4.226 Hakem: A R Hall  |
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| 19 Kasım 1999 | Luton Town | 2 - 2 | Lincoln City | Kenilworth Road, Luton |
|  | Doherty  63', 84' |  | Gordon  14' Barnett  81' | Stadyum: Kenilworth Road, Luton  Seyirci: 4.291 Hakem: Stephen Lodge  |
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| 30 Kasım 1999 | Lincoln City | 0 - 1 | Luton Town | Sincil Bank, Lincoln |
|  |  |  | Douglas  85' | Stadyum: Sincil Bank, Lincoln  Seyirci: 3.822 Hakem: Stephen Lodge  |
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| 20 Kasım 1999 | Oldham Athletic | 1 - 0 | Swansea City | Boundary Park, Oldham |
|  | Whitehall  45' |  |  | Stadyum: Boundary Park, Oldham  Seyirci: 4.332 Hakem: M Fletcher  |
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| 20 Kasım 1999 | Plymouth Argyle | 0 - 0 | Brighton & Hove Albion | Home Park, Plymouth |
|  |  |  | Freeman  61' Cullip  76' | Stadyum: Home Park, Plymouth  Seyirci: 7.414 Hakem: Rob Harris  |
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| 30 Kasım 1999 | Brighton & Hove Albion | 1 - 2 | Plymouth Argyle | Withdean Stadyumu, Brighton |
|  | Cullip  63' |  | Bastow  9' Hargreaves  65' | Stadyum: Withdean Stadyumu, Brighton  Seyirci: 5.710 Hakem: Stephen Lodge  |
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| 20 Kasım 1999 | Preston North End | 0 - 0 | Enfield | Deepdale, Preston |
|  |  |  |  | Stadyum: Deepdale, Preston  Seyirci: 11.566 Hakem: P Rejer  |
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| 30 Kasım 1999 | Enfield | 0 - 3 | Preston North End | Goldsdown Road, Enfield |
|  | Protheroe  60' |  | Eyres  52' Alexander  60' (pen.) Gunnlaugsson  83' | Stadyum: Goldsdown Road, Enfield  Seyirci: 1.808 Hakem: P Rejer  |
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| 20 Kasım 1999 | Reading | 1 - 1 | Halifax Town | Madejski Stadyumu, Reading |
|  | Caskey  75' (pen.) Parkinson  39' |  | Mitchell  60' | Stadyum: Madejski Stadyumu, Reading  Seyirci: 5.918 Hakem: Richard Beeby  |
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| 30 Kasım 1999 | Halifax Town | 0 - 1 | Reading | The Shay, Halifax |
|  |  |  | Caskey  74' (pen.) Polston  90' | Stadyum: The Shay, Halifax  Seyirci: 2.156 Hakem: Richard Beeby  |
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| 20 Kasım 1999 | Shrewsbury Town | 2 - 2 | Oxford United | Gay Meadow, Shrewsbury |
|  | Kerrigan  8', 54' |  | Murphy  63' Folland  77' | Stadyum: Gay Meadow, Shrewsbury  Seyirci: 3.357 Hakem: T Jones  |
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| 30 Kasım 1999 | Oxford United | 2 - 1 (uz.) | Shrewsbury Town | Manor Ground, Oxford |
|  | Murphy  90', 117' |  | Jagielka  27' | Stadyum: Manor Ground, Oxford  Seyirci: 4.096 Hakem: T Jones  |
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| 20 Kasım 1999 | Stalybridge Celtic | 1 - 2 | Chester City | Bower Fold, Stalybridge |
|  | Scott  8' Parr  90' |  | Cross  45' Beckett  69' | Stadyum: Bower Fold, Stalybridge  Seyirci: 3.312 Hakem: Michael Ryan  |
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| 20 Kasım 1999 | Wrexham | 2 - 1 | Rochdale | Racecourse Ground, Wrexham |
|  | Roberts  5' Faulconbridge  88' |  | Atkinson  33' | Stadyum: Racecourse Ground, Wrexham  Seyirci: 3.408 Hakem: Trevor Parkes  |
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| 20 Kasım 1999 | Wycombe Wanderers | 2 - 2 | Wigan Athletic | Causeway Stadyumu, Wycombe |
|  | Devine  20' Ryan  90' |  | Haworth  45', 61' | Stadyum: Causeway Stadyumu, Wycombe  Seyirci: 2.992 Hakem: R Olivier  |
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| 30 Kasım 1999 | Wigan Athletic | 2 - 1 | Wycombe Wanderers | JJB Stadyumu, Wigan |
|  | Liddell  28' Haworth  80' |  | Baird  23' | Stadyum: JJB Stadyumu, Wigan  Seyirci: 3.967 Hakem: R Olivier  |