Football Association Challenge Cup 1899–1900 var den 29. udgave af Football Association Challenge Cup, nutildags bedre kendt som FA Cup. Turneringen blev afviklet som en cupturnering med deltagelse af 237 klubber. De første kampe blev spillet den 16. september 1899, og finalen blev afviklet den 21. april 1900 på Crystal Palace i London, hvor Bury FC besejrede Southampton FC med 4-0. Det var første gang, at Bury FC vandt FA Cup'en, og begge finalister var i FA Cup-finalen for første gang. Southampton FC spillede i den sæson i Southern League, og det var første gang siden oprettelsen af The Football League i 1888, at et hold uden for denne liga kvalificerede sig til finalen i FA Cup'en.
Resultater
Bury FC's vej til sejren
RundeDatoKampRes.Første runde 27.1.Burnley FC – Bury FC 0–1Anden runde 10.2.Notts County FC – Bury FC 0–0 14.2.Bury FC – Notts County FC 2–0Kvartfinale 24.2.Sheffield United FC – Bury FC 2–2 1.3.Bury FC – Sheffield United FC 2–0Semifinale 24.3.Bury FC – Nottingham Forest FC 1–1 29.3.Bury FC – Nottingham Forest FC 3–2Finale 21.4.Bury FC – Southampton FC 4–0
Indledende runde
Den indledende runde havde deltagelse af 76 hold, der spillede om 38 ledige pladser i første kvalifikationsrunde.
DatoKampRes.16.9.Ashington FC – St. Peter's Albion FC 0–1Blackburn Park Road FC – Accrington Stanley FC 3–0Middleton FC – Rochdale FC 2–0Nuneaton Town FC – Brierley Hill Alliance FC 2–3Prudhoe FC – Mickley FC 1–123.9.Ashford United FC – Folkestone FC 1–0Attercliffe FC – Montrose Works FC 3–0Barking Woodville FC – West Ham Garfield FC 0–1Bromley FC – Deptford Town FC 0–2Clapton FC – Leyton FC 4–1Darlington FC – Tow Law FC 2–0Darlington St. Augustines FC – Bishop Auckland FC 2–9Darwen FC – Great Harwood FC 1–1Denaby United FC – Parkgate United FC 1–0Desborough Town FC – Wellingborough Town FC 0–5Dover FC – Sittingbourne FC 2–1Grangetown Athletic FC – Thornaby FC 0–3Grays United FC – Royal Scots Fusiliers FC 0–0Ilford FC – Romford FC 6–0Leadgate Park FC – Howden-le-Wear FC 2–1Leytonstone FC – Olympic FC 2–4London Welsh FC – Queens Park Rangers FC 2–4Maidstone United FC – Dartford FC 1–2DatoKampRes.23.9.Mexborough FC – Pyebank FC 6–0FC Nelson – Trawden Forest FC 2–1New Brighton Tower FC – Birkenhead FC 5–0Oswaldtwistle Rovers FC – Hapton FC 3–1Redhill FC – West Croydon FC 4–2Rushden FC – Rothwell Town Swifts FC 4–0Sheppey United FC – Gravesend United FC 3–1South Liverpool FC – White Star Wanderers FC 3–0Thames Ironworks FC – Royal Engineers United FC 6–0Thornaby Utopians FC – South Bank FC 3–3Upton Park FC – Olympian FC 4–1Whitby FC – Stockton FC 4–0Winsford United FC – 1st South Lancashire Regiment FC 1–1Worthing FC – Eastbourne Town FC 0–1 –Birtley FC – Seaham Albion FC w.o.Omkampe 20.9.South Bank FC – Thornaby Utopians FC 3–1 21.9.Mickley FC – Prudhoe FC 3–1 26.9.Great Harwood FC – Darwen FC 0–627.9.Royal Scots Fusiliers FC – Grays United FC 1–31st South Lancashire Regiment FC – Winsford United FC 0–1
Første kvalifikationsrunde
Første kvalifikationsrunde havde deltagelse af 116 hold, der spillede om 58 ledige pladser i anden kvalifikationsrunde. 38 af holdene var vindere fra den indledende runde, mens de resterende 78 hold trådte ind i turneringen i første kvalifikationsrunde.
DatoKampRes.30.9.Aberystwyth FC – Newtown AFC 5–7Attercliffe FC – Mexborough FC 1–1Aylesbury United FC – Chesham Generals FC 3–0Brighton United FC – Eastbourne Town FC 6–1Bristol East FC – Staple Hill FC 2–0Burton Wanderers FC – Swadlincote FC 2–0Clapton FC – Olympic FC 4–0Coalville Town FC – Gresley FC 3–0Colchester Town FC – Norwich CEYMS FC 2–4Congleton Hornets FC – Buxton FC 3–1Crook Town FC – Darlington FC 1–1Dartford FC – Ashford United FC 1–0Darwen FC – Blackburn Park Road FC 3–2Denaby United FC – Sheffield FC 1–1Deptford Town FC – Wandsworth FC 1–4Dudley Town FC – Brierley Hill Alliance FC 8–2Dunstable Thursdays FC – Wolverton LNWR FC 0–5Eastbourne Swifts FC – Brighton Athletic FC 1–3Finedon Revellers FC – Rushden FC 2–4Gainsborough Trinity FC – Doncaster Rovers FC 1–4Gateshead NER FC – Birtley FC 4–0Heywood FC – Walshaw FC 1–2Hunslet FC – Altofts FC 3–0Ilford FC – Upton Park FC 3–1Ilkeston Town FC – Chesterfield FC 1–2Ironbridge FC – Wellington AFC 2–2Kirkley & Pakefield FC – Harwich & Parkeston FC 2–1Leadgate Park FC – Bishop Auckland FC 2–2Maidenhead FC – Maidenhead Norfolkians FC 2–4Nantwich FC – Winsford United FC 2–1New Brighton Tower FC – Wirral Railway FC 7–1Newstead Byron FC – Bulwell United FC 2–0Northampton Town FC – Wellingborough Town FC 1–2Oswaldtwistle Rovers FC – FC Nelson FC 3–0DatoKampRes.30.9.Portsmouth FC – Ryde FC 10–0Queens Park Rangers FC – Fulham FC 3–0Reading Ramblers FC – Oxford City FC 1–1Redhill FC – West Norwood FC 2–4Richmond Association FC – 1st Scots Guards FC 2–0Seaham Harbour FC – South Shields FC 0–5St. Peter's Albion FC – Shankhouse FC 0–1Stapleford Town FC – Belper Town FC 14–0Stockton St. John's FC – South Bank FC 0–2Stourbridge FC – Coventry City FC 5–0Swanscombe FC – Dover FC 5–2Thames Ironworks FC – Grays United FC 4–0Thornaby FC – Whitby FC 2–0Tranmere Rovers FC – South Liverpool FC 0–1Wallsend Park Villa FC – Mickley FC 2–1Warrington St. Elphin's FC – Middlewitch Rangers FC 5–1Watford FC – Hitchin FC 7–1Wath Athletic FC – Wombwell Town FC 1–2West Ham Garfield FC – Sheppey United FC 1–8West Hampstead FC – Hampstead FC 10–0Wigan County FC – Swinton Town FC 8–0Workington FC – Black Diamonds FC 6–0Worksop Town FC – Newark FC 1–1 –Freetown FC – Middleton FC w.o.Omkampe 2.10.Wellington AFC – Ironbridge FC 1–04.10.Bishop Auckland FC – Leadgate Park FC 5–1Darlington FC – Crook Town AFC 2–3Oxford City FC – Reading Ramblers FC 1–35.10.Mexborough FC – Attercliffe FC 2–0Newark FC – Worksop Town FC 1–0Sheffield FC – Danaby United FC 0–1
Anden kvalifikationsrunde
Anden kvalifikationsrunde havde deltagelse af 79 hold, der spillede om 40 ledige pladser i tredje kvalifikationsrunde. På grund af det ulige antal hold var Blackpool FC oversidder og gik derfor videre til tredje kvalifikationsrunde uden kamp. 58 af holdene var vindere fra første kvalifikationsrunde, mens de resterende 21 hold først trådte ind i turneringen i anden kvalifikationsrunde.
DatoKampRes.14.10.Bishop Auckland FC – Crook Town AFC 3–2Brighton United FC – Brighton Athletic FC 9–0Bristol East FC – Bristol Amateurs FC 1–0Burton Wanderers FC – Coalville Town FC 0–2Chesham Town FC – Aylesbury United FC 2–0Chesterfield FC – Stapleford Town FC 5–2Clapton FC – Ilford FC 2–1Denaby United FC – Mexborough FC 2–1Doncaster Rovers FC – Newark FC 3–1Eastleigh Athletic FC – Freemantle FC 5–0Freetown FC – Walshaw FC 2–1Gateshead NER FC – South Shields FC 1–0Haydock FC – Wigan County FC 1–4Hinckley Town FC – Barwell Swifts FC 7–1Hucknall Portland FC – Newstead Byron FC 3–2Llandudno Swifts FC – Wrexham AFC 1–2Moss Bay Exchange FC – Workington FC 1–1Nantwich FC – Warrington St. Elphin's FC 2–1Norwich CEYMS FC – Kirkley & Parkfield FC 1–0Oswaldtwistle Rovers FC – Darwen FC 2–2Oswestry United FC – Newtown AFC 3–3Portsmouth FC – Cowes FC 3–2Queens Park Rangers FC – West Hampstead FC 5–0DatoKampRes.14.10.Reading Ramblers FC – Oxford Cygnets FC 4–2Shephers Bush FC – Richmond Association FC 2–3Shrewsbury Town FC – Wellington AFC 1–2Slough FC – Maidenhead Norfolkians FC 2–2South Bank FC – Thornaby FC 0–2South Liverpool FC – New Brighton Tower FC 3–2Stalybridge Rovers FC – Congleton Hornets FC 2–0Stourbridge FC – Dudley Town FC 1–4Swanscombe FC – Dartford FC 1–2Thames Ironworks FC – Sheppey United FC 4–2Wallsend Park Villa FC – Shankhouse FC 6–0Watford FC – Wolverton LNWR FC 1–0Wellingborough Town FC – Rushden FC 1–1West Norwood FC – Wandsworth FC 0–1Wombwell Town FC – Hunslet FC 1–2Yeovil Casuals FC – Street FC 3–3Omkampe19.10.Maidenhead Norfolkians FC – Slough FC 4–0Newtown AFC – Oswestry United FC 1–3Rushden FC – Wellingborough Town FC 1–321.10.Darwen FC – Oswaldtwistle Rovers FC 4–0Workington FC – Moss Bay Exchange FC 6–1 –Street FC – Yeovil Casuals FC w.o.
Tredje kvalifikationsrunde
Tredje kvalifikationsrunde havde deltagelse af 80 hold, der spillede om 40 ledige pladser i fjerde kvalifikationsrunde. 40 af holdene var vindere fra anden kvalifikationsrunde, mens de resterende 40 hold først trådte ind i turneringen i tredje kvalifikationsrunde.
DatoKampRes.28.10.Barnsley FC – Lincoln City FC 1–0Blackpool FC – Southport Central FC 0–2Brentford FC – Ridhmond Associaiton FC | 1–2|- | style="text-align:left; padding-left:5px;"|Bristol East FC – Street FC | 4–1|- | style="text-align:left; padding-left:5px;"|Bristol Rovers FC – Eastleigh Athletic FC | 5–0|- | style="text-align:left; padding-left:5px;"|Burslem Port Vale FC – Nantwich FC | 2–0|- | style="text-align:left; padding-left:5px;"|Burton Swifts FC – Kettering FC | 8–2|- | style="text-align:left; padding-left:5px;"|Chatham FC – Brighton United FC | 2–0|- | style="text-align:left; padding-left:5px;"|Chesham Town FC – Maidenhead Norfolkians FC | 11–3|- | style="text-align:left; padding-left:5px;"|Chesterfield FC – Heanor Town FC | 6–1|- | style="text-align:left; padding-left:5px;"|Chorley FC – Workington FC | 6–1|- | style="text-align:left; padding-left:5px;"|Coalville Town FC – Hucknall Portland FC | 3–3|- | style="text-align:left; padding-left:5px;"|Crewe Alexandra FC – Wigan County FC | 3–1|- | style="text-align:left; padding-left:5px;"|Crouch End Vampires FC – Watford FC| 0–3|- | style="text-align:left; padding-left:5px;"|Dartford FC – Thames Ironworks FC| 0–7|- | style="text-align:left; padding-left:5px;"|Darwen FC – Freetown FC | 3–1|- | style="text-align:left; padding-left:5px;"|Denaby United FC – Hunslet FC | 2–2|- | style="text-align:left; padding-left:5px;"|Gateshead NER FC – Bishop Auckland FC | 1–1|- | style="text-align:left; padding-left:5px;"|Glossop AFC – Stockport County FC | 2–2|- | style="text-align:left; padding-left:5px;"|Grimsby Town FC – Doncaster Rovers FC | 3–1|- | style="text-align:left; padding-left:5px;"|Leicester Fosse FC – Wellingborough Town FC | 3–1|- | style="text-align:left; padding-left:5px;"|Loughborough FC – Hinckley Town FC| 1–2|- | style="text-align:left; padding-left:5px;"|Lowestoft Town FC – Luton Town FC| 0–2|- | style="text-align:left; padding-left:5px;"|Marlow FC – Reading Ramblers FC | 4–2|- | style="text-align:left; padding-left:5px;"|Middlesbrough FC – Jarrow FC| 1–2|- | style="text-align:left; padding-left:5px;"|Millwall Athletic FC – Clapton FC | 7–0|- | style="text-align:left; padding-left:5px;"|Norwich CEYMS FC – Civil Service FC| 1–3'''DatoKampRes.28.10.Portsmouth FC – Swindon Town FC 2–1Queens Park Rangers FC – Wandsworth FC 7–1Small Heath FC – Oswestry United FC 10–2South Shore FC – Newton Heath FC 3–1Stalybridge Rovers FC – South Liverpool FC 1–0Wallsend Park Villa FC – Hebburn Argyle FC 1–1Walsall FC – Kidderminster Harriers FC 6–1Wellington AFC – Druids FC 4–0Weymouth FC – Bedminster FC 0–6Willington Athletic FC – Thornaby FC 5–0Woolwich Arsenal FC – New Brompton FC 1–1Wrexham AFC – Dudley Town FC 3–2Wycombe Wanderers FC – Reading FC 0–8Omkampe1.11.Bishop Auckland FC – Gateshead NER FC 4–0Hebburn Argyle FC – Wallsend Park Villa FC 2–3Hunslet FC – Denaby United FC 1–1New Brompton FC – Woolwich Arsenal FC 0–0Stockport County FC – Glossop AFC 3–0 2.11.Hucknall Portland FC – Coalville Town FC 4–3Anden omkamp6.11.Hunslet FC – Denaby United FC 4–3New Brompton FC – Woolwich Arsenal FC 2–2Tredje omkamp 8.11.New Brompton FC – Woolwich Arsenal FC 1–1Fjerde omkamp 14.11.New Brompton FC – Woolwich Arsenal FC 1–0
Fjerde kvalifikationsrunde
Fjerde kvalifikationsrunde havde deltagelse af 40 de vinderhold fra tredje kvalifikationsrunde, der spillede om 20 ledige pladser i femte kvalifikationsrunde.