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| F.A. Cup | |||||||||||
| 1998/99 Results | |||||||||||
| * denotes non-league club | |||||||||||
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| First Round | |||||||||||
| Sat | Nov | 14 | Basingstoke Town* | 1 | - | 2 | Bournemouth | ||||
| Sat | Nov | 14 | Bedlington Terriers* | 4 | - | 1 | Colchester United | ||||
| Sun | Nov | 15 | Boreham Wood* | 2 | - | 3 | Luton Town | ||||
| Sat | Nov | 14 | Brentford | 5 | - | 0 | Camberley Town* | ||||
| Sat | Nov | 14 | Bristol Rovers | 3 | - | 0 | Welling United | ||||
| Sat | Nov | 14 | Cardiff City | 6 | - | 0 | Chester City | ||||
| Sat | Nov | 14 | Cheltenham Town* | 0 | - | 1 | Lincoln City | ||||
| Tue | Nov | 17 | Darlington | 3 | - | 2 | Burnley | ||||
| (the match was played at the Riverside Stadium, Middlesbrough FC) | |||||||||||
| Sat | Nov | 14 | Dulwich Hamlet* | 0 | - | 1 | Southport* | ||||
| Sun | Nov | 15 | Emley* | 1 | - | 1 | Rotherham United | ||||
| (the match was played at Oakwell, Barnsley FC) | |||||||||||
| Tue | Nov | 24 | Rotherham United | 3 | - | 1 |
Emley* |
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| Sat | Nov | 14 | Enfield* | 2 | - | 2 | York City | ||||
| Tue | Nov | 24 | York City | 2 | - | 1 |
Enfield* |
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| Sun | Nov | 15 | Fulham | 1 | - | 1 | Leigh RMI* | ||||
| Tue | Nov | 24 | Leigh RMI* | 0 | - | 2 |
Fulham |
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| Sat | Nov | 14 | Hartlepool United | 2 | - | 1 | Carlisle United | ||||
| Sat | Nov | 14 | Hednesford Town* | 3 | - | 1 | Barnet | ||||
| Sun | Nov | 15 | Hendon* | 0 | - | 0 | Notts County | ||||
| Tue | Dec | 1 | Notts County | 3 | - | 0 |
Hendon* |
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| Sat | Nov | 14 | Kingstonian* | 1 | - | 0 | Burton Albion* | ||||
| Sat | Nov | 14 | Leyton Orient | 4 | - | 2 | Brighton & Hove Albion | ||||
| Sat | Nov | 14 | Macclesfield Town | 2 | - | 2 | Slough Town* | ||||
| Tue | Nov | 24 | Slough Town* | 1 | - | 1 |
Macclesfield Town |
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| (Macclesfield Town won 9-8 on penalties) | |||||||||||
| Fri | Nov | 13 | Manchester City | 3 | - | 0 | Halifax Town | ||||
| Sat | Nov | 14 | Mansfield Town | 2 | - | 1 | Hayes* | ||||
| Sat | Nov | 14 | Northampton Town | 2 | - | 1 | Lancaster City* | ||||
| Sat | Nov | 14 | Oldham Athletic | 2 | - | 0 | Gillingham | ||||
| Sat | Nov | 14 | Plymouth Argyle | 0 | - | 0 | Kidderminster Harriers* | ||||
| Tue | Nov | 24 | Kidderminster Harriers* | 0 | - | 0 |
Plymouth Argyle |
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| (fog caused an abandonment at half-time - match void) | |||||||||||
| Tue | Dec | 1 | Kidderminster Harriers* | 0 | - | 0 |
Plymouth Argyle |
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| (Plymouth Argyle won 5-4 on penalties) | |||||||||||
| Sat | Nov | 14 | Preston North End | 3 | - | 0 | Ford United* | ||||
| Sat | Nov | 14 | Reading | 0 | - | 1 | Stoke City | ||||
| Sat | Nov | 14 | Runcorn* | 1 | - | 1 | Stevenage Borough* | ||||
| Mon | Nov | 23 | Stevenage Borough* | 2 | - | 0 |
Runcorn* |
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| Sat | Nov | 14 | Rushden & Diamonds* | 1 | - | 0 | Shrewsbury Town | ||||
| Sat | Nov | 14 | Salisbury City* | 0 | - | 2 | Hull City | ||||
| Sat | Nov | 14 | Scarborough | 1 | - | 1 | Rochdale | ||||
| Tue | Nov | 24 | Rochdale | 2 | - | 0 |
Scarborough |
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| Sat | Nov | 14 | Southend United | 0 | - | 1 | Doncaster Rovers* | ||||
| Fri | Nov | 13 | Swansea City | 3 | - | 0 | Millwall | ||||
| Sat | Nov | 14 | Tamworth* | 2 | - | 2 | Exeter City | ||||
| Tue | Nov | 24 | Exeter City | 4 | - | 1 |
Tamworth* |
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| Sat | Nov | 14 | Telford United* | 0 | - | 2 | Cambridge United | ||||
| Sat | Nov | 14 | Walsall | 1 | - | 0 | Gresley Rovers* | ||||
| Sat | Nov | 14 | Wigan Athletic | 4 | - | 3 | Blackpool | ||||
| Sat | Nov | 14 | Woking* | 0 | - | 1 | Scunthorpe United | ||||
| Sat | Nov | 14 | Worcester City* | 0 | - | 1 | Torquay United | ||||
| Sat | Nov | 14 | Wrexham | 1 | - | 0 | Peterborough United | ||||
| Sat | Nov | 14 | Wycombe Wanderers | 1 | - | 0 | Chesterfield | ||||
| Sat | Nov | 14 | Yeovil Town* | 2 | - | 2 | West Auckland Town* | ||||
| Tue | Nov | 24 | West Auckland Town* | 1 | - | 1 |
Yeovil Town* |
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| (Yeovil Town won 5-3 on penalties) | |||||||||||
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| Second Round | |||||||||||
| Sat | Dec | 5 | Cardiff City | 3 | - | 1 | Hednesford Town* | ||||
| Fri | Dec | 4 | Darlington | 1 | - | 1 | Manchester City | ||||
| Tue | Dec | 15 | Manchester City | 1 | - | 0 |
Darlington |
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| Sat | Dec | 5 | Doncaster Rovers* | 0 | - | 0 | Rushden & Diamonds* | ||||
| Tue | Dec | 15 | Rushden & Diamonds* | 4 | - | 2 |
Doncaster Rovers* |
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| Sat | Dec | 5 | Exeter City | 2 | - | 2 | Bristol Rovers | ||||
| Tue | Dec | 15 | Bristol Rovers | 5 | - | 0 |
Exeter City |
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| Sat | Dec | 5 | Fulham | 4 | - | 2 | Hartlepool United | ||||
| Sun | Dec | 6 | Kingstonian* | 0 | - | 0 | Leyton Orient | ||||
| Tue | Dec | 15 | Leyton Orient | 2 | - | 1 |
Kingstonian* |
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| Sat | Dec | 5 | Lincoln City | 4 | - | 1 | Stevenage Borough* | ||||
| Sat | Dec | 5 | Luton Town | 1 | - | 2 | Hull City | ||||
| Sat | Dec | 5 | Macclesfield Town | 4 | - | 1 | Cambridge United | ||||
| Sat | Dec | 5 | Mansfield Town | 1 | - | 2 | Southport* | ||||
| Sat | Dec | 5 | Notts County | 1 | - | 1 | Wigan Athletic | ||||
| Tue | Dec | 15 | Wigan Athletic | 0 | - | 0 |
Notts County |
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| (Notts County won 4-2 on penalties) | |||||||||||
| Sat | Dec | 5 | Oldham Athletic | 1 | - | 1 | Brentford | ||||
| Tue | Dec | 15 | Brentford | 2 | - | 2 |
Oldham Athletic |
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| (Oldham Athletic won 4-2 on penalties) | |||||||||||
| Sat | Dec | 5 | Preston North End | 2 | - | 0 | Walsall | ||||
| Sat | Dec | 5 | Rochdale | 0 | - | 0 | Rotherham United | ||||
| Tue | Dec | 15 | Rotherham United | 4 | - | 0 |
Rochdale |
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| Sat | Dec | 5 | Scunthorpe United | 2 | - | 0 | Bedlington Terriers* | ||||
| Sat | Dec | 5 | Swansea City | 1 | - | 0 | Stoke City | ||||
| Sat | Dec | 5 | Torquay United | 0 | - | 1 | Bournemouth | ||||
| Sat | Dec | 5 | Wrexham | 2 | - | 1 | York City | ||||
| Sat | Dec | 5 | Wycombe Wanderers | 1 | - | 1 | Plymouth Argyle | ||||
| Tue | Dec | 15 | Plymouth Argyle | 3 | - | 2 |
Wycombe Wanderers |
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| Sat | Dec | 5 | Yeovil Town* | 2 | - | 0 | Northampton Town | ||||
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| Third Round | |||||||||||
| Sat | Jan | 2 | Aston Villa | 3 | - | 0 | Hull City | ||||
| Sat | Jan | 2 | Blackburn Rovers | 2 | - | 0 | Charlton Athletic | ||||
| Sat | Jan | 2 | Bolton Wanderers | 1 | - | 2 | Wolverhampton Wanderers | ||||
| Sat | Jan | 2 | Bournemouth | 1 | - | 0 | West Bromwich Albion | ||||
| Sat | Jan | 2 | Bradford City | 2 | - | 1 | Grimsby Town | ||||
| Sat | Jan | 2 | Bristol City | 0 | - | 2 | Everton | ||||
| Sat | Jan | 2 | Bury | 0 | - | 3 | Stockport County | ||||
| Sat | Jan | 2 | Cardiff City | 1 | - | 1 | Yeovil Town* | ||||
| Tue | Jan | 12 | Yeovil Town* | 1 | - | 2 |
Cardiff City |
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| Sat | Jan | 2 | Coventry City | 7 | - | 0 | Macclesfield Town | ||||
| Sat | Jan | 2 | Crewe Alexandra | 1 | - | 3 | Oxford United | ||||
| Sat | Jan | 2 | Leicester City | 4 | - | 2 | Birmingham City | ||||
| Sat | Jan | 2 | Lincoln City | 0 | - | 1 | Sunderland | ||||
| Sun | Jan | 3 | Manchester United | 3 | - | 1 | Middlesbrough | ||||
| Sat | Jan | 2 | Newcastle United | 2 | - | 1 | Crystal Palace | ||||
| Sat | Jan | 2 | Nottingham Forest | 0 | - | 1 | Portsmouth | ||||
| Sat | Jan | 2 | Oldham Athletic | 0 | - | 2 | Chelsea | ||||
| Sat | Jan | 2 | Plymouth Argyle | 0 | - | 3 | Derby County | ||||
| Sun | Jan | 3 | Port Vale | 0 | - | 3 | Liverpool | ||||
| Mon | Jan | 4 | Preston North End | 2 | - | 4 | Arsenal (holders) | ||||
| Sat | Jan | 2 | Queens Park Rangers | 0 | - | 1 | Huddersfield Town | ||||
| Sat | Jan | 2 | Rotherham United | 0 | - | 1 | Bristol Rovers | ||||
| Sat | Jan | 2 | Rushden & Diamonds* | 0 | - | 0 | Leeds United | ||||
| Wed | Jan | 13 | Leeds United | 3 | - | 1 |
Rushden & Diamonds* |
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| Sat | Jan | 2 | Sheffield United | 1 | - | 1 | Notts County | ||||
| Sat | Jan | 23 | Notts County | 3 | - | 4 |
Sheffield United |
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| Sun | Jan | 3 | Sheffield Wednesday | 4 | - | 1 | Norwich City | ||||
| Sat | Jan | 2 | Southampton | 1 | - | 1 | Fulham | ||||
| Wed | Jan | 13 | Fulham | 1 | - | 0 |
Southampton |
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| Sat | Jan | 2 | Southport* | 0 | - | 2 | Leyton Orient | ||||
| Sat | Jan | 2 | Swindon Town | 0 | - | 0 | Barnsley | ||||
| Tue | Jan | 19 | Barnsley | 3 | - | 1 |
Swindon Town |
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| Sat | Jan | 2 | Tottenham Hotspur | 5 | - | 2 | Watford | ||||
| Sat | Jan | 2 | Tranmere Rovers | 0 | - | 1 | Ipswich Town | ||||
| Sat | Jan | 2 | West Ham United | 1 | - | 1 | Swansea City | ||||
| Wed | Jan | 13 | Swansea City | 1 | - | 0 |
West Ham United |
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| Sat | Jan | 2 | Wimbledon | 1 | - | 0 | Manchester City | ||||
| Sat | Jan | 2 | Wrexham | 4 | - | 3 | Scunthorpe United | ||||
| Fourth Round | |||||||||||
| Sat | Jan | 23 | Aston Villa | 0 | - | 2 | Fulham | ||||
| Sat | Jan | 23 | Barnsley | 3 | - | 1 | Bournemouth | ||||
| Sat | Jan | 23 | Blackburn Rovers | 1 | - | 0 | Sunderland | ||||
| Sat | Jan | 23 | Bristol Rovers | 3 | - | 0 | Leyton Orient | ||||
| Sat | Jan | 23 | Everton | 1 | - | 0 | Ipswich Town | ||||
| Sat | Jan | 23 | Leicester City | 0 | - | 3 | Coventry City | ||||
| Sun | Jan | 24 | Manchester United | 2 | - | 1 | Liverpool | ||||
| Sat | Jan | 23 | Newcastle United | 3 | - | 0 | Bradford City | ||||
| Mon | Jan | 25 | Oxford United | 1 | - | 1 | Chelsea | ||||
| Wed | Feb | 3 | Chelsea | 4 | - | 2 |
Oxford United |
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| Sat | Jan | 23 | Portsmouth | 1 | - | 5 | Leeds United | ||||
| Wed | Jan | 27 | Sheffield United | 4 | - | 1 | Cardiff City | ||||
| Sat | Jan | 23 | Sheffield Wednesday | 2 | - | 0 | Stockport County | ||||
| Sat | Jan | 23 | Swansea City | 0 | - | 1 | Derby County | ||||
| Sat | Jan | 23 | Wimbledon | 1 | - | 1 | Tottenham Hotspur | ||||
| Tue | Feb | 2 | Tottenham Hotspur | 3 | - | 0 |
Wimbledon |
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| Sun | Jan | 24 | Wolverhampton Wanderers | 1 | - | 2 | Arsenal (holders) | ||||
| Sat | Jan | 23 | Wrexham | 1 | - | 1 | Huddersfield Town | ||||
| Wed | Feb | 3 | Huddersfield Town | 2 | - | 1 |
Wrexham |
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| Fifth Round | |||||||||||
| Sat | Feb | 13 | Arsenal (holders) | 2 | - | 1 | Sheffield United | ||||
| (this result was declared void - see note) | |||||||||||
| Tue | Feb | 23 | Arsenal (holders) | 2 | - | 1 |
Sheffield United |
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| Sat | Feb | 13 | Barnsley | 4 | - | 1 | Bristol Rovers | ||||
| Sat | Feb | 13 | Everton | 2 | - | 1 | Coventry City | ||||
| Sat | Feb | 13 | Huddersfield Town | 2 | - | 2 | Derby County | ||||
| Wed | Feb | 24 | Derby County | 3 | - | 1 |
Huddersfield Town |
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| Sat | Feb | 13 | Leeds United | 1 | - | 1 | Tottenham Hotspur | ||||
| Wed | Feb | 24 | Tottenham Hotspur | 2 | - | 0 |
Leeds United |
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| Sun | Feb | 14 | Manchester United | 1 | - | 0 | Fulham | ||||
| Sun | Feb | 14 | Newcastle United | 0 | - | 0 | Blackburn Rovers | ||||
| Wed | Feb | 24 | Blackburn Rovers | 0 | - | 1 |
Newcastle United |
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| Sat | Feb | 13 | Sheffield Wednesday | 0 | - | 1 | Chelsea | ||||
| Sixth Round | |||||||||||
| Sat | Mar | 6 | Arsenal (holders) | 1 | - | 0 | Derby County | ||||
| Tue | Mar | 16 | Barnsley | 0 | - | 1 | Tottenham Hotspur | ||||
| Sun | Mar | 7 | Manchester United | 0 | - | 0 | Chelsea | ||||
| Wed | Mar | 10 | Chelsea | 0 | - | 2 |
Manchester United |
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| Sun | Mar | 7 | Newcastle United | ||||||||
