| Final |
| 17.5.99 |
| Newcastle United |
v
|
Manchester United |
| Semi Final Replay |
| |
| Manchester United |
2-1
|
Arsenal |
| Semi Finals |
| |
| Manchester United |
0-0
|
Arsenal |
| Newcastle United |
2-0
|
Tottenham Hotspur |
| Quarter Final Replay |
| |
| Chelsea |
0-2
|
Manchester United |
| Quarter Finals |
| |
| Arsenal |
1-0
|
Derby County |
| Barnsley |
0-1
|
Tottenham Hotspur |
| Manchester United |
0-0
|
Chelsea |
| Newcastle United |
4-1
|
Everton |
| Fifth Round Replays |
| |
| Arsenal |
2-1
|
Sheffield Utd |
| Blackburn |
0-1
|
Newcastle United |
| Derby County |
3-1
|
Huddersfield Town |
| Tottenham Hotspur |
2-0
|
Leeds |
| Fifth Round |
| |
| Arsenal |
2-1
|
Sheffield Utd |
| Barnsley |
4-1
|
Bristol Rovers |
| Everton |
2-1
|
Coventry |
| Leeds |
1-1
|
Tottenham Hotspur |
| Newcastle United |
0-0
|
Blackburn |
| Manchester United |
1-0
|
Fulham |
| Sheffield Wednesday |
0-1
|
Chelsea |
| Huddersfield Town |
2-2
|
Derby County |
| Fourth Round Replays |
| |
| Tottenham Hotspur |
3-0
|
Wimbledon |
| Chelsea |
4-2
|
Oxford United |
| Huddersfield Town |
2-1
|
Wrexham |
| Fourth Round |
| |
| Aston Villa |
0-2
|
Fulham |
| Barnsley |
3-1
|
Bournemouth |
| Blackburn Rovers |
1-0
|
Sunderland |
| Bristol Rovers |
3-0
|
Leyton Orient |
| Everton |
1-0
|
Ipswich Town |
| Leicester City |
0-3
|
Coventry City |
| Manchester United |
2-1
|
Liverpool |
| Newcastle United |
3-0
|
Bradford City |
| Oxford United |
1-1
|
Chelsea |
| Portsmouth |
1-5
|
Leeds United |
| Sheffield Wednesday |
2-0
|
Stockport County |
| Sheffield United |
4-1
|
Cardiff City |
| Swansea City |
0-1
|
Derby County |
| Wimbledon |
1-1
|
Tottenham Hotspur |
| Wolverhampton W |
1-2
|
Arsenal |
| Wrexham |
1-1
|
Huddersfield Town |
| Third Round Replays |
| |
| Barnsley |
3-1
|
Swindon Town |
| Fulham |
1-0
|
Southampton |
| Leeds United |
3-1
|
Rushden & Diamonds |
| Notts County |
3-4
|
Sheffield United |
| Swansea City |
1-0
|
West Ham United |
| Yeovil |
1-2
|
Cardiff City |
| Third Round |
| |
| Aston Villa |
3-0
|
Hull City |
| Bury |
0-3
|
Stockport County |
| Blackburn Rovers |
2-0
|
Charlton Athletic |
| Bolton Wanderers |
1-2
|
Wolverhampton W |
| Bournemouth |
1-0
|
West Bromwich Albion |
| Bradford City |
2-1
|
Grimsby Town |
| Bristol City |
0-2
|
Everton |
| Coventry City |
7-0
|
Macclesfield Town |
| Crewe Alexandra |
1-3
|
Oxford United |
| Leicester City |
4-2
|
Birmingham City |
| Lincoln City |
0-1
|
Sunderland |
| Manchester United |
3-1
|
Middlesbrough |
| Newcastle United |
2-1
|
Crystal Palace |
| Nottingham Forest |
0-1
|
Portsmouth |
| Oldham Athletic |
0-2
|
Chelsea |
| Plymouth Argyle |
0-3
|
Derby County |
| Port Vale |
0-3
|
Liverpool |
| Preston North End |
2-4
|
Arsenal |
| Queens Park Rangers |
0-1
|
Huddersfield Town |
| Rotherham United |
0-1
|
Bristol Rovers |
| Sheffield United |
1-1
|
Notts County |
| Sheffield Wednesday |
4-1
|
Norwich City |
| Southport |
0-2
|
Leyton Orient |
| Tottenham Hotspur |
5-2
|
Watford |
| Tranmere Rovers |
0-1
|
Ipswich Town |
| Wimbledon |
1-0
|
Manchester City |
| Wrexham |
4-3
|
Scunthorpe United |
| Second Round Replays |
| |
| Brentford |
2-2
|
Oldham Athletic |
| Oldham Athletic win 4-2 on penalties |
| Bristol Rovers |
5-0
|
Exeter City |
| Leyton Orient |
2-1
|
Kingstonian |
| Manchester City |
1-0
|
Darlington |
| Plymouth Argyle |
3-2
|
Wycombe Wanderers |
| Rotherham United |
4-0
|
Rochdale |
| Rushden & Diamonds |
4-2
|
Doncaster Rovers |
| Wigan Athletic |
0-0
|
Notts County |
| Notts County win 4-2 on penalties |
| Second Round |
| |
| Cardiff City |
3-1
|
Hednesford |
| Darlington |
1-1
|
Manchester City |
| Doncaster Rovers |
0-0
|
Rushden & Diamonds |
| Exeter City |
2-2
|
Bristol Rovers |
| Fulham |
4-2
|
Hartlepool |
| Kingstonian |
0-0
|
Leyton Orient |
| Lincoln City |
4-1
|
Stevenage |
| Luton Town |
1-2
|
Hull City |
| Macclesfield Town |
4-1
|
Cambridge United |
| Mansfield Town |
1-2
|
Southport |
| Notts County |
1-1
|
Wigan Athletic |
| Oldham Athletic |
1-1
|
Brentford |
| Preston North End |
2-0
|
Walsall |
| Rochdale |
0-0
|
Rotherham United |
| Scunthorpe United |
2-0
|
Bedlington Terriers |
| Swansea City |
1-0
|
Stoke City |
| Torquay United |
0-1
|
Bournemouth |
| Wrexham |
2-1
|
York City |
| Wycombe Wanderers |
1-1
|
Plymouth Argyle |
| Yeovil |
2-0
|
Northampton Town |
| First Round Replays |
| |
| Exeter City |
4-1
|
Tamworth |
| Kidderminster |
0-0
|
Plymouth Argyle |
| Plymouth win 5-4 on penalties |
| Leigh RMI |
0-2
|
Fulham |
| Notts County |
3-0
|
Hendon |
| Rochdale |
2-0
|
Scarborough |
| Rotherham United |
3-1
|
Emley |
| Stevenage |
2-0
|
Runcorn |
| Slough Town |
1-1
|
Macclesfield Town |
| Macclesfield Town win 9-8 on penalties |
| West Auckland |
1-1
|
Yeovil |
| Yeovil win 5-3 on penalties |
| York City |
2-1
|
Enfield |
| First Round |
| |
| Basingstoke |
1-2
|
Bournemouth |
| Bedlington Terriers |
4-1
|
Colchester United |
| Boreham Wood |
2-3
|
Luton Town |
| Brentford |
5-0
|
Camberley Town |
| Bristol Rovers |
3-0
|
Welling |
| Cardiff City |
6-0
|
Chester City |
| Cheltenham |
0-1
|
Lincoln City |
| Darlington |
3-2
|
Burnley |
| Dulwich |
0-1
|
Southport |
| Emley |
1-1
|
Rotherham United |
| Enfield |
2-2
|
York City |
| Fulham |
1-1
|
Leigh RMI |
| Hartlepool United |
2-1
|
Carlisle United |
| Hednesford |
3-1
|
Barnet |
| Hendon |
0-0
|
Notts County |
| Kingstonian |
1-0
|
Burton Albion |
| Leyton Orient |
4-2
|
Brighton & Hove Albion |
| Macclesfield Town |
2-2
|
Slough |
| Manchester City |
3-0
|
Halifax Town |
| Mansfield Town |
2-1
|
Hayes |
| Northampton Town |
2-1
|
Lancaster |
| Oldham Athletic |
2-0
|
Gillingham |
| Plymouth Argyle |
0-0
|
Kidderminster Harriers |
| Preston North End |
3-0
|
Ford United |
| Reading |
0-1
|
Stoke City |
| Runcorn |
1-1
|
Stevenage |
| Rushden & Diamonds |
1-0
|
Shrewsbury |
| Salisbury |
0-2
|
Hull City |
| Scarborough |
1-1
|
Rochdale |
| Southend United |
0-1
|
Doncaster Rovers |
| Swansea City |
3-0
|
Millwall |
| Tamworth |
2-2
|
Exeter City |
| Telford |
0-2
|
Cambridge United |
| Walsall |
1-0
|
Gresley Rovers |
| Wigan Athletic |
4-3
|
Blackpool |
| Woking |
0-1
|
Scunthorpe United |
| Worcester |
0-1
|
Torquay United |
| Wrexham |
1-0
|
Peterborough United |
| Wycombe Wanderers |
1-0
|
Chesterfield |
| Yeovil |
2-2
|
West Auckland |
|
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