Football Association Challenge Cup 1898–99 var den 28. udgave af Football Association Challenge Cup, nu til dags bedre kendt som FA Cup. Turneringen blev afviklet som en cupturnering med deltagelse af 236 klubber. De første kampe blev spillet den 17. september 1898, og finalen blev afviklet den 15. april 1899 på Crystal Palace i London, hvor Sheffield United FC besejrede Derby County FC med 4-1. Det var første gang, at Sheffield United vandt FA Cup'en – og det var også første gang at klubben overhovedet nåede finalen. Til gengæld tabte Derby County i finalen for anden sæson i træk.

Resultater

Sheffield Uniteds vej til sejren

RundeDatoKampRes.Første runde 28.1.Burnley FC – Sheffield United FC 2–2 1.2.Sheffield United FC – Burnley FC 2–1Anden runde 11.2.Preston North End FC – Sheffield United FC 2–2 16.2.Sheffield United FC – Preston North End FC 2–1Kvartfinale 25.2.Nottingham Forest FC – Sheffield United FC 0–1Semifinale 18.3.Liverpool FC – Sheffield United FC 2–2 23.3.Liverpool FC – Sheffield United FC 4–4 27.3.Liverpool FC – Sheffield United FC 1–0 30.3.Sheffield United FC – Liverpool FC 1–0Finale 15.4.Sheffield United FC – Derby County FC 4–1

Indledende runde

Den indledende runde havde deltagelse af 62 hold, der spillede om 31 ledige pladser i første kvalifikationsrunde.

DatoKampRes.17.9.Brighton United FC – Romford FC 8–2Hapton FC – South Shore FC 0–5Hebburn Argyle FC – Seaham Harbour FC 1–024.9.1st Coldstream Guards FC – Barnet FC 4–3Aberystwyth FC – Middlewich Rangers FC 4–1Aylesbury United FC – Harwich & Parkeston FC 3–2Carlisle City FC – Trawden Forest FC 2–3Chatham FC – London Welsh FC 5–0Crook Town AFC – Shankhouse FC 4–1Folkestone FC – Faversham FC 2–1Hounslow FC – Shepherds Bush FC 1–3Ilford FC – Civil Service FC 2–0Leyton FC – Swanscombe FC 1–1Maidenhead FC – 2nd Coldstream Guards FC 2–0Newbury FC – Bedminster FC 0–3Richmond Association FC – Queens Park Rangers FC 3–0Royal Engineers Training Battalion FC – Eastbourne Swifts FC 6–2Rutherford College FC – Bishop Auckland FC 0–1DatoKampRes.24.9.Sittingbourne FC – Wandsworth FC 2–1South Shields FC – Shildon United FC 3–1St. Albans FC – Crouch End Vampires FC 2–2St. Peter's Albion FC – Thornaby FC 1–0Staple Hill FC – Eastleigh Athletic FC 2–1Tow Law FC – Darlington St. Augustines FC 2–0Uxbridge FC – Hitchin FC 0–2Watford FC – Chesham Town FC 1–0West Norwood FC – Bromley FC 3–3Wolverton LNWR FC – Windsor & Eton FC 8–0Wycombe Wanderers FC – Marlow FC 1–2–3rd Grenadier Guards FC – Hampstead FC w.o.Norwich CEYMS FC – Slough FC w.o.Omkampe28.9.Crouch End Vampires FC – St. Albans FC 2–4Swanscombe FC – Leyton FC 1–1 29.9.Bromley FC – West Norwood FC 3–0Anden omkamp 1.10.Leyton FC – Swanscombe FC 2–1

Første kvalifikationsrunde

Første kvalifikationsrunde havde deltagelse af 126 hold, der spillede om 63 ledige pladser i anden kvalifikationsrunde. 31 af holdene var vindere fra den indledende runde, mens de resterende 95 hold først trådte ind i turneringen i første kvalifikationsrunde.

DatoKampRes.24.9.Eastville Wanderers FC – Oxford City FC 1–3Workington FC – Rossendale United FC 3–1 28.9.Burton Swifts FC – Hugglescote Robin Hood FC 4–11.10.3rd Grenadier Guards FC – 1st Coldstream Guards FC 2–2Aberystwyth FC – 1st South Lancashire Regiment FC 0–2Altofts FC – Attercliffe FC 0–0Ashton North End FC – Rhyl United FC 13–1Aylesbury United FC – Hitchin FC 5–1Bedminster FC – Ryde FC 3–1Birkenhead LNWR FC – Bangor City FC 0–1Birtley FC – Thornaby Utopians FC 6–0Bishop Auckland FC – Crook Town AFC 6–0Black Diamonds FC – Trawden Forest FC 1–3Brighton United FC – Ashford United FC 5–0Bulwell United FC – Finedon Revellers FC 9–1Congleton Hornets FC – Hurst Ramblers FC 2–0Coventry City FC – Hereford FC 0–0Cowes FC – Trowbridge Town FC 7–1Eastbourne Town FC – Sittingbourne FC 0–0Freemantle FC – Andover FC 2–0Freetown FC – Halliwell Rovers FC 0–2Frizington White Star FC – Fleetwood Rangers FC 3–0Halesowen FC – Wellington AFC 2–8Hinckley Town FC – Northampton Town FC 1–2Hindley FC – Blackburn Park Road FC 6–1Horwich FC – South Shore FC 0–1Howden-le-Wear FC – Mickley FC 2–2Leadgate Exiles FC – Gateshead NER FC 2–3Leadgate Park FC – Hebburn Argyle FC 0–1Leytonstone FC – Chatham FC 3–1Loughborough FC – Mansfield FC 4–0Lowestoft Town FC – Norwich CEYMS FC 3–0Maidstone United FC – Folkestone FC 1–0Marlow FC – 3rd Coldstream Guards FC 3–1Middleton FC – Rochdale FC 3–2Newtown AFC – Druids FC 0–2Oswaldtwistle Rovers FC – Accrington Stanley FC 2–4Oxford Cygnets FC – Warmley FC 2–9DatoKampRes.1.10.Parkgate United FC – Sheffield FC 2–0Reading Ramblers FC – Bristol St. George FC 1–10Richmond Association FC – Ilford FC 2–0Rothwell Town Swifts FC – Newark FC 1–0Royal Artillery Portsmouth FC – Weymouth FC 5–0Seaham Albion FC – South Shields FC 0–6South Bank FC – Willington Athletic FC 1–2Southport Central FC – Blackpool FC 2–2St. Albans FC – Shepherds Bush FC 1–2St. Peter's Albion FC – Tow Law FC 1–0Stalybridge Rovers FC – Garston Copper Works FC 4–0Staple Hill FC – Chippenham Town FC 7–0Stourbridge FC – Shrewsbury Town FC 2–1Swadlincote FC – Langley Mill Rangers FC 3–0Swinton Town FC – Worksop Town FC 0–3Thames Ironworks FC – Royal Engineers Training Battalion FC 2–0Upton Park FC – Metropolitan Railway FC 0–3Warrington St. Elphin's FC – South Liverpool FC 0–6Watford FC – Chesham Generals FC 4–0Wath-upon-Dearne FC – Hunslet FC 1–1West Croydon FC – Bromley FC 0–1Wrexham AFC – Chester FC 3–2 8.10.Leyton FC – Grays United FC 0–1–Welshpool FC – Kidderminster Harriers FC w.o.Wolverton LNWR FC – Maidenhead FC w.o.Omkampe5.10.Hunslet FC – Wath-upon-Dearne FC 0–0Sittingbourne FC – Eastbourne Town FC 4–26.10.3rd Grenadier Guards FC – 1st Coldstream Guards FC 4–0Attercliffe FC – Altofts FC 2–1Blackpool FC – Southport Central FC 1–2Hereford FC – Coventry City FC 1–0 12.10.South Shore FC – Horwich FC 2–0 –Mickley FC – Howden-le-Wear FC w.o.Anden omkamp 10.10.Wath-upon-Dearne FC – Hunslet FC 3–3Tredje omkamp 12.10.Hunslet FC – Wath-upon-Dearne FC 1–2

Anden kvalifikationsrunde

Anden kvalifikationsrunde havde deltagelse af 80 hold, der spillede om 40 ledige pladser i tredje kvalifikationsrunde. 63 af holdene var vindere fra første kvalifikationsrunde, mens de resterende 17 hold først trådte ind i turneringen i anden kvalifikationsrunde.

DatoKampRes.15.10.1st South Lancashire Regiment FC – Congleton Hornets FC 2–2Accrington Stanley FC – Frizington White Star FC 8–0Bangor City FC – Ashton North End FC 2–1Kampen blev beordret spillet om.Barwell Swifts FC – Kimberley FC 4–4Bradford FC – Parkgate United FC 2–2Brighton United FC – Thames Ironworks FC 0–0Bristol St. George FC – Staple Hill FC 4–1Burton Swifts FC – Coalville Town FC 4–1Doncaster Rovers FC – Wath-upon-Dearne FC 6–0Freemantle FC – Oxford City FC 2–1Grays United FC – Sittingbourne FC 4–0Halliwell Rovers FC – South Shore FC 1–1Heanor Town FC – Gresley FC 4–0Hebburn Argyle FC – Birtley FC 1–1Hindley FC – Workington FC 2–4Hucknall Portland FC – Bulwell United FC 2–2Ironbridge FC – Druids FC 1–1Leytonstone FC – Maidstone United FC 2–3Loughborough FC – Rothwell Town Swifts FC 7–0Metropolitan Railway FC – Bromley FC 3–2Richmond Association FC – Marlow FC 4–3Royal Artillery Portsmouth FC – Cowes FC 1–1Shepherds Bush FC – Aylesbury United FC 2–0South Liverpool FC – Wrexham AFC 4–2South Shields FC – Bishop Auckland FC 2–0South Shields FC blev diskvalificeret.Southport Central FC – Trawden Forest FC 3–2St. Peter's Albion FC – Mickley FC 2–1Stalybridge Rovers FC – Middleton FC | 3–6'''DatoKampRes.15.10.Stapleford Town FC – Coalville Albion FC 4–1Swadlincote FC – Belper Town FC 2–1Warmley FC – Bedminster FC 1–1Watford FC – Lowestoft Town FC 2–0Wellingborough Town FC – Northampton Town FC 0–2Welshpool FC – Chirk AAA FC 1–3Willington Athletic FC – Gateshead NER FC 2–1Wolverton LNWR FC – 3rd Grenadier Guards FC 3–0Wombwell Town FC – Barnsley FC 0–1Worksop Town FC – Attercliffe FC 0–1–Oswestry United FC – Stourbridge FC w.o.Wellington AFC – Hereford FC w.o.Omkampe19.10.Bedminster FC – Warmley FC 2–2Birtley FC – Hebburn Argyle FC 0–2Congleton Hornets FC – 1st South Lancashire Regiment FC 3–4Druids FC – Ironbridge FC 5–1Kimberley FC – Barwell Swifts FC 7–0Parkgate United FC – Bradford FC 8–4Thames Ironworks FC – Brighton United FC 1–420.10.Bulwell United FC – Hucknall Portland FC 5–2Cowes FC – Royal Artillery Portsmouth FC 3–0 24.10.Wellingborough Town FC – Northampton Town FC 6–1 25.10.Workington FC – Hindley FC 4–0–Ashton North End FC – Bangor City FC w.o.South Shore FC – Halliwell Rovers FC w.o.Anden omkamp 24.10.Warmley FC – Bedminster FC 2–1

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.29.10.Ashton North End FC – Stockport County FC 2–2Bishop Auckland FC – Darlington FC 4–1Bristol Rovers FC – Reading FC 0–1Bristol St. George FC – Freemantle FC 7–0Burslem Port Vale FC – Wellington AFC 5–0Burton Swifts FC – Ilkeston Town FC 4–2Burton Wanderers FC – Oswestry United FC 7–2Chesterfield FC – Swadlincote FC 8–0Chorley FC – Workington FC 5–1Clapton FC – Brentford FC 6–1Cowes FC – Bristol City FC 0–5Crewe Alexandra FC – South Liverpool FC 4–1Darwen FC – Wigan County FC 1–5Doncaster Rovers FC – Parkgate United FC 8–1Druids FC – Walsall FC 2–1Gainsborough Trinity FC – Barnsley FC 2–2Glossop AFC – New Brighton Tower FC 4–2Gravesend United FC – Metropolitan Railway FC 8–2Grimsby Town FC – Mexborough FC 5–0Heanor Town FC – Long Eaton Rangers FC 3–2Jarrow FC – St. Peter's Albion FC 1–0Leicester Fosse FC – Kimberley FC 9–0Lincoln City FC – Attercliffe FC 5–0Loughborough FC – Wellingborough Town FC 0–0DatoKampRes.29.10.Luton Town FC – Watford FC 2–2Maidstone United FC – Sheppey United FC 2–5Middlesbrough FC – Hebburn Argyle FC 0–1Middleton FC – 1st South Lancashire Regiment FC 3–0Millwall Athletic FC – Brighton United FC 3–0New Brompton FC – Grays United FC 3–0Rushden FC – Bulwell United FC 4–2Shepherds Bush FC – Richmond Association FC 0–0Small Heath FC – Chirk AAA FC 8–0South Shore FC – Accrington Stanley FC 5–1Southport Central FC – FC Nelson 3–0Stapleford Town FC – Buxton FC 5–1Tottenham Hotspur FC – Wolverton LNWR FC 4–0Warmley FC – Swindon Town FC 1–0Willington Athletic FC – Stockton FC 5–1 3.11.Kettering FC – Hucknall St. John's FC 1–0Omkampe 31.10.Wellingborough Town FC – Loughborough FC 1–3 2.11.Watford FC – Luton Town FC 0–13.11.Barnsley FC – Gainsborough Trinity FC 4–0Richmond Association FC – Shepherds Bush FC 0–2Stockport County FC – Ashton North End FC 1–0

Fjerde kvalifikationsrunde

Fjerde kvalifikationsrunde havde deltagelse af de 40 vinderhold fra tredje kvalifikationsrunde, der spillede om 20 ledige pladser i femte kvalifikationsrunde.

DatoKampRes.19.11.Bishop Auckland FC – Jarrow FC 1–2Bristol St. George FC – Bristol City FC 0–1Burslem Port Vale FC – Burton Wanderers FC 3–0Burton Swifts FC – Chesterfield FC 1–0Clapton FC – Tottenham Hotspur FC 1–1Doncaster Rovers FC – Barnsley FC 1–2Glossop AFC – Crewe Alexandra FC 1–0Gravesend United FC – Millwall Athletic FC 3–1Grimsby Town FC – Lincoln City FC 2–1Kettering FC – Loughborough FC 2–1Leicester Fosse FC – Rushden FC 2–1Luton Town FC – Shepherds Bush FC 4–3DatoKampRes.19.11.New Brompton FC – Sheppey United FC 2–1Reading FC – Warmley FC 1–1Small Heath FC – Druids FC 10–0South Shore FC – Chorley FC 1–0Southport Central FC – Wigan County FC 3–1Stapleford Town FC – Heanor Town FC 1–3Stockport County FC – Middleton FC 3–0Willington Athletic FC – Hebburn Argyle FC 1–2Omkampe 23.11.Tottenham Hotspur FC – Clapton FC 2–1 30.11.Reading FC – Warmley FC 3–0

Femte kvalifikationsrunde

Femte kvalifikationsrunde havde deltagelse af de 20 vinderhold fra fjerde kvalifikationsrunde, der spillede om 10 ledige pladser i første runde.