First Round | ||||||
|---|---|---|---|---|---|---|
| 13 Nov 1998 | Manchester City | 3:0 | Halifax Town | |||
| 13 Nov 1998 | Swansea City | 3:0 | Millwall | |||
| 14 Nov 1998 | Basingstoke Town | 1:2 | AFC Bournemouth | |||
| 14 Nov 1998 | Bedlington Terriers | 4:1 | Colchester United | |||
| 14 Nov 1998 | Brentford | 5:0 | Camberley Town | |||
| 14 Nov 1998 | Bristol Rovers | 3:0 | Welling United | |||
| 14 Nov 1998 | Cardiff City | 6:0 | Chester City | |||
| 14 Nov 1998 | Cheltenham Town | 0:1 | Lincoln City | |||
| 14 Nov 1998 | Dulwich Hamlet | 0:1 | Southport | |||
| 14 Nov 1998 | Enfield | 2:2 | York City | |||
| 14 Nov 1998 | Hartlepool United | 2:1 | Carlisle United | |||
| 14 Nov 1998 | Hednesford | 3:1 | Barnet | |||
| 14 Nov 1998 | Kingstonian | 1:0 | Burton Albion | |||
| 14 Nov 1998 | Leyton Orient | 4:2 | Brighton and Hove Albion | |||
| 14 Nov 1998 | Macclesfield Town | 2:2 | Slough Town | |||
| 14 Nov 1998 | Mansfield Town | 2:1 | Hayes | |||
| 14 Nov 1998 | Northampton Town | 2:1 | Lancaster | |||
| 14 Nov 1998 | Oldham Athletic | 2:0 | Gillingham | |||
| 14 Nov 1998 | Plymouth Argyle | 0:0 | Kidderminster Harriers | |||
| 14 Nov 1998 | Preston North End | 3:0 | Ford United | |||
| 14 Nov 1998 | Reading | 0:1 | Stoke City | |||
| 14 Nov 1998 | Runcorn | 1:1 | Stevenage Borough | |||
| 14 Nov 1998 | Rushden and Diamonds | 1:0 | Shrewsbury Town | |||
| 14 Nov 1998 | Salisbury City | 0:2 | Hull City | |||
| 14 Nov 1998 | Scarborough | 1:1 | Rochdale | |||
| 14 Nov 1998 | Southend United | 0:1 | Doncaster Rovers | |||
| 14 Nov 1998 | Tamworth | 2:2 | Exeter City | |||
| 14 Nov 1998 | Telford | 0:2 | Cambridge United | |||
| 14 Nov 1998 | Walsall | 1:0 | Gresley Rovers | |||
| 14 Nov 1998 | Wigan Athletic | 4:3 | Blackpool | |||
| 14 Nov 1998 | Woking | 0:1 | Scunthorpe United | |||
| 14 Nov 1998 | Worcester City | 0:1 | Torquay United | |||
| 14 Nov 1998 | Wrexham | 1:0 | Peterborough United | |||
| 14 Nov 1998 | Wycombe Wanderers | 1:0 | Chesterfield | |||
| 14 Nov 1998 | Yeovil Town | 2:2 | West Auckland Town | |||
| 15 Nov 1998 | Boreham Wood | 2:3 | Luton Town | |||
| 15 Nov 1998 | Emley | 1:1 | Rotherham United | |||
| 15 Nov 1998 | Fulham | 1:1 | Leigh RMI | |||
| 15 Nov 1998 | Hendon | 0:0 | Notts County | |||
| 17 Nov 1998 | Darlington | 3:2 | Burnley | |||
| 23 Nov 1998 | Stevenage Borough | 2:0 | Runcorn | replay | ||
| 24 Nov 1998 | Exeter City | 4:1 | Tamworth | replay | ||
| 24 Nov 1998 | Leigh RMI | 0:2 | Fulham | replay | ||
| 24 Nov 1998 | Rochdale | 2:0 | Scarborough | replay | ||
| 24 Nov 1998 | Rotherham United | 3:1 | Emley | replay | ||
| 24 Nov 1998 | Slough Town | 1:1 (8:9) | Macclesfield Town | replay | ||
| 24 Nov 1998 | West Auckland Town | 1:1 (3:5) | Yeovil Town | replay | ||
| 24 Nov 1998 | York City | 2:1 | Enfield | replay | ||
| 01 Dec 1998 | Kidderminster Harriers | 0:0 (4:5) | Plymouth Argyle | replay | ||
| 01 Dec 1998 | Notts County | 3:0 | Hendon | replay | ||
Second Round | ||||||
| 04 Dec 1998 | Darlington | 1:1 | Manchester City | |||
| 05 Dec 1998 | Cardiff City | 3:1 | Hednesford | |||
| 05 Dec 1998 | Doncaster Rovers | 0:0 | Rushden and Diamonds | |||
| 05 Dec 1998 | Exeter City | 2:2 | Bristol Rovers | |||
| 05 Dec 1998 | Fulham | 4:2 | Hartlepool United | |||
| 05 Dec 1998 | Lincoln City | 4:1 | Stevenage Borough | |||
| 05 Dec 1998 | Luton Town | 1:2 | Hull City | |||
| 05 Dec 1998 | Macclesfield Town | 4:1 | Cambridge United | |||
| 05 Dec 1998 | Mansfield Town | 1:2 | Southport | |||
| 05 Dec 1998 | Notts County | 1:1 | Wigan Athletic | |||
| 05 Dec 1998 | Oldham Athletic | 1:1 | Brentford | |||
| 05 Dec 1998 | Preston North End | 2:0 | Walsall | |||
| 05 Dec 1998 | Rochdale | 0:0 | Rotherham United | |||
| 05 Dec 1998 | Scunthorpe United | 2:0 | Bedlington Terriers | |||
| 05 Dec 1998 | Swansea City | 1:0 | Stoke City | |||
| 05 Dec 1998 | Torquay United | 0:1 | AFC Bournemouth | |||
| 05 Dec 1998 | Wrexham | 2:1 | York City | |||
| 05 Dec 1998 | Wycombe Wanderers | 1:1 | Plymouth Argyle | |||
| 05 Dec 1998 | Yeovil Town | 2:0 | Northampton Town | |||
| 06 Dec 1998 | Kingstonian | 0:0 | Leyton Orient | |||
| 15 Dec 1998 | Brentford | 2:2 (2:4) | Oldham Athletic | replay | ||
| 15 Dec 1998 | Bristol Rovers | 5:0 | Exeter City | replay | ||
| 15 Dec 1998 | Leyton Orient | 2:1 | Kingstonian | replay | ||
| 15 Dec 1998 | Manchester City | 1:0 | Darlington | replay | ||
| 15 Dec 1998 | Plymouth Argyle | 3:2 | Wycombe Wanderers | replay | ||
| 15 Dec 1998 | Rotherham United | 4:0 | Rochdale | replay | ||
| 15 Dec 1998 | Rushden and Diamonds | 4:2 | Doncaster Rovers | replay | ||
| 15 Dec 1998 | Wigan Athletic | 0:0 (2:4) | Notts County | replay | ||
Third Round | ||||||
| 02 Jan 1999 | AFC Bournemouth | 1:0 | West Bromwich Albion | |||
| 02 Jan 1999 | Aston Villa | 3:0 | Hull City | |||
| 02 Jan 1999 | Blackburn Rovers | 2:0 | Charlton Athletic | |||
| 02 Jan 1999 | Bolton Wanderers | 1:2 | Wolverhampton Wanderers | |||
| 02 Jan 1999 | Bradford City | 2:1 | Grimsby Town | |||
| 02 Jan 1999 | Bristol City | 0:2 | Everton | |||
| 02 Jan 1999 | Bury | 0:3 | Stockport County | |||
| 02 Jan 1999 | Cardiff City | 1:1 | Yeovil Town | |||
| 02 Jan 1999 | Coventry City | 7:0 | Macclesfield Town | |||
| 02 Jan 1999 | Crewe Alexandra | 1:3 | Oxford United | |||
| 02 Jan 1999 | Leicester City | 4:2 | Birmingham City | |||
| 02 Jan 1999 | Lincoln City | 0:1 | Sunderland | |||
| 02 Jan 1999 | Newcastle United | 2:1 | Crystal Palace | |||
| 02 Jan 1999 | Nottingham Forest | 0:1 | Portsmouth | |||
| 02 Jan 1999 | Oldham Athletic | 0:2 | Chelsea | |||
| 02 Jan 1999 | Plymouth Argyle | 0:3 | Derby County | |||
| 02 Jan 1999 | Queens Park Rangers | 0:1 | Huddersfield Town | |||
| 02 Jan 1999 | Rotherham United | 0:1 | Bristol Rovers | |||
| 02 Jan 1999 | Rushden and Diamonds | 0:0 | Leeds United | |||
| 02 Jan 1999 | Sheffield United | 1:1 | Notts County | |||
| 02 Jan 1999 | Southampton | 1:1 | Fulham | |||
| 02 Jan 1999 | Southport | 0:2 | Leyton Orient | |||
| 02 Jan 1999 | Swindon Town | 0:0 | Barnsley | |||
| 02 Jan 1999 | Tottenham Hotspur | 5:2 | Watford | |||
| 02 Jan 1999 | Tranmere Rovers | 0:1 | Ipswich Town | |||
| 02 Jan 1999 | West Ham United | 1:1 | Swansea City | |||
| 02 Jan 1999 | Wimbledon | 1:0 | Manchester City | |||
| 02 Jan 1999 | Wrexham | 4:3 | Scunthorpe United | |||
| 03 Jan 1999 | Manchester United | 3:1 | Middlesbrough | |||
| 03 Jan 1999 | Port Vale | 0:3 | Liverpool | |||
| 03 Jan 1999 | Sheffield Wednesday | 4:1 | Norwich City | |||
| 04 Jan 1999 | Preston North End | 2:4 | Arsenal | |||
| 12 Jan 1999 | Yeovil Town | 1:2 | Cardiff City | replay | ||
| 13 Jan 1999 | Fulham | 1:0 | Southampton | replay | ||
| 13 Jan 1999 | Leeds United | 3:1 | Rushden and Diamonds | replay | ||
| 13 Jan 1999 | Swansea City | 1:0 | West Ham United | replay | ||
| 19 Jan 1999 | Barnsley | 3:1 | Swindon Town | replay | ||
| 23 Jan 1999 | Notts County | 3:4 | Sheffield United | replay | ||
Fourth Round | ||||||
| 23 Jan 1999 | Aston Villa | 0:2 | Fulham | |||
| 23 Jan 1999 | Barnsley | 3:1 | AFC Bournemouth | |||
| 23 Jan 1999 | Blackburn Rovers | 1:0 | Sunderland | |||
| 23 Jan 1999 | Bristol Rovers | 3:0 | Leyton Orient | |||
| 23 Jan 1999 | Everton | 1:0 | Ipswich Town | |||
| 23 Jan 1999 | Leicester City | 0:3 | Coventry City | |||
| 23 Jan 1999 | Newcastle United | 3:0 | Bradford City | |||
| 23 Jan 1999 | Portsmouth | 1:5 | Leeds United | |||
| 23 Jan 1999 | Sheffield Wednesday | 2:0 | Stockport County | |||
| 23 Jan 1999 | Swansea City | 0:1 | Derby County | |||
| 23 Jan 1999 | Wimbledon | 1:1 | Tottenham Hotspur | |||
| 23 Jan 1999 | Wrexham | 1:1 | Huddersfield Town | |||
| 24 Jan 1999 | Manchester United | 2:1 | Liverpool | |||
| 24 Jan 1999 | Wolverhampton Wanderers | 1:2 | Arsenal | |||
| 25 Jan 1999 | Oxford United | 1:1 | Chelsea | |||
| 27 Jan 1999 | Sheffield United | 4:1 | Cardiff City | |||
| 02 Feb 1999 | Tottenham Hotspur | 3:0 | Wimbledon | replay | ||
| 03 Feb 1999 | Chelsea | 4:2 | Oxford United | replay | ||
| 03 Feb 1999 | Huddersfield Town | 2:1 | Wrexham | replay | ||
Fifth Round | ||||||
| 13 Feb 1999 | Barnsley | 4:1 | Bristol Rovers | |||
| 13 Feb 1999 | Everton | 2:1 | Coventry City | |||
| 13 Feb 1999 | Huddersfield Town | 2:2 | Derby County | |||
| 13 Feb 1999 | Leeds United | 1:1 | Tottenham Hotspur | |||
| 13 Feb 1999 | Sheffield Wednesday | 0:1 | Chelsea | |||
| 14 Feb 1999 | Manchester United | 1:0 | Fulham | |||
| 14 Feb 1999 | Newcastle United | 0:0 | Blackburn Rovers | |||
| 23 Feb 1999 | Arsenal | 2:1 | Sheffield United | |||
| 24 Feb 1999 | Blackburn Rovers | 0:1 | Newcastle United | replay | ||
| 24 Feb 1999 | Derby County | 3:1 | Huddersfield Town | replay | ||
| 24 Feb 1999 | Tottenham Hotspur | 2:0 | Leeds United | replay | ||
Quarter-finals | ||||||
| 06 Mar 1999 | Arsenal | 1:0 | Derby County | |||
| 07 Mar 1999 | Manchester United | 0:0 | Chelsea | |||
| 07 Mar 1999 | Newcastle United | 4:1 | Everton | |||
| 10 Mar 1999 | Chelsea | 0:2 | Manchester United | replay | ||
| 16 Mar 1999 | Barnsley | 0:1 | Tottenham Hotspur | |||
Semi-finals | ||||||
| 11 Apr 1999 | Manchester United | 0:0 | Arsenal | |||
| 11 Apr 1999 | Newcastle United | 2:0 | Tottenham Hotspur | |||
| 14 Apr 1999 | Arsenal | 1:2 | Manchester United | replay | ||
Final | ||||||
| 22 May 1999 | Manchester United | 2:0 | Newcastle United | |||