22nd May 1999
| Final | Manchester United | 2-0 | Newcastle United |
14th April 1999
| Semi Final Replay | Manchester United | 2-1 | Arsenal |
11th April 1999
| Semi Final | Manchester United | 0-0 | Arsenal |
| Semi Final | Newcastle United | 2-0 | Tottenham Hotspur |
16th March 1999
| 6th Round | Barnsley | 0-1 | Tottenham Hotspur |
10th March 1999
| 6th Round Replay | Chelsea | 0-2 | Manchester United |
7th March 1999
| 6th Round | Manchester United | 0-0 | Chelsea |
| 6th Round | Newcastle United | 4-1 | Everton |
6th March 1999
| 6th Round | Arsenal | 1-0 | Derby County |
24th February 1999
| 5th Round Replay | Blackburn Rovers | 0-1 | Newcastle United |
| 5th Round Replay | Derby County | 3-1 | Huddersfield Town |
| 5th Round Replay | Tottenham Hotspur | 2-0 | Leeds United |
23rd February 1999
| 5th Round Replay | Arsenal | 2-1 | Sheffield United |
14th February 1999
| 5th Round | Manchester United | 1-0 | Fulham |
| 5th Round | Newcastle United | 0-0 | Blackburn Rovers |
13th February 1999
| 5th Round | Arsenal | 2-1 | Sheffield United |
| 5th Round | Barnsley | 4-1 | Bristol Rovers |
| 5th Round | Everton | 2-1 | Coventry City |
| 5th Round | Huddersfield Town | 2-2 | Derby County |
| 5th Round | Leeds United | 1-1 | Tottenham Hotspur |
| 5th Round | Sheffield Wednesday | 0-1 | Chelsea |
3rd February 1999
| 4th Round Replay | Chelsea | 4-2 | Oxford United |
| 4th Round Replay | Huddersfield Town | 2-1 | Wrexham |
2nd February 1999
| 4th Round Replay | Tottenham Hotspur | 3-0 |
27th January 1999
| 4th Round | Sheffield United | 4-1 | Cardiff City |
25th January 1999
| 4th Round | Oxford United | 1-1 | Chelsea |
24th January 1999
| 4th Round | Manchester United | 2-1 | Liverpool |
| 4th Round | Wolverhampton Wanderers | 1-2 | Arsenal |
23rd January 1999
| 3rd Round Replay | Notts. County | 3-4 | Sheffield United |
| 4th Round | Aston Villa | 0-2 | Fulham |
| 4th Round | Barnsley | 3-1 | AFC Bournemouth |
| 4th Round | Blackburn Rovers | 3-1 | Sunderland |
| 4th Round | Bristol Rovers | 3-0 | Leyton Orient |
| 4th Round | Everton | 1-0 | Ipswich Town |
| 4th Round | Leicester City | 0-3 | Coventry City |
| 4th Round | Newcastle United | 3-0 | Bradford City |
| 4th Round | Portsmouth | 1-5 | Leeds United |
| 4th Round | Sheffield Wednesday | 2-0 |
| 4th Round | Swansea City | 0-1 | Derby County |
| 4th Round | 1-1 | Tottenham Hotspur |
| 4th Round | Wrexham | 1-1 | Huddersfield Town |
19th January 1999
| 3rd Round Replay | Barnsley | 3-1 | Swindon Town |
13th January 1999
| 3rd Round Replay | Fulham | 1-0 | Southampton |
| 3rd Round Replay | Leeds United | 3-1 |
| 3rd Round Replay | Swansea City | 1-0 | West Ham United |
12th January 1999
| 3rd Round Replay | 1-2 | Cardiff City |
4th January 1999
| 3rd Round | Preston North End | 2-4 | Arsenal |
3rd January 1999
| 3rd Round | Manchester United | 3-1 | Middlesbrough |
| 3rd Round | Port Vale | 0-3 | Liverpool |
| 3rd Round | Sheffield Wednesday | 4-1 | Norwich City |
2nd January 1999
| 3rd Round | Aston Villa | 3-0 | Hull City |
| 3rd Round | Blackburn Rovers | 2-0 | Charlton Athletic |
| 3rd Round | Bolton Wanderers | 1-2 | Wolverhampton Wanderers |
| 3rd Round | AFC Bournemouth | 1-0 | West Bromwich Albion |
| 3rd Round | Bradford City | 2-1 | Grimsby Town |
| 3rd Round | Bristol City | 0-2 | Everton |
| 3rd Round | 0-3 |
| 3rd Round | Cardiff City | 1-1 |
| 3rd Round | Coventry City | 7-0 | Macclesfield Town |
| 3rd Round | Crewe Alexandra | 1-3 | Oxford United |
| 3rd Round | Leicester City | 4-2 | Birmingham City |
| 3rd Round | Lincoln City | 0-1 | Sunderland |
| 3rd Round | Newcastle United | 2-1 | Crystal Palace |
| 3rd Round | Nottingham Forest | 0-1 | Portsmouth |
| 3rd Round | Oldham Athletic | 0-2 | Chelsea |
| 3rd Round | Plymouth Argyle | 0-3 | Derby County |
| 3rd Round | Queens Park Rangers | 0-1 | Huddersfield Town |
| 3rd Round | Rotherham United | 0-1 | Bristol Rovers |
| 3rd Round | 0-0 | Leeds United |
| 3rd Round | Sheffield United | 1-1 | Notts. County |
| 3rd Round | Southampton | 1-1 | Fulham |
| 3rd Round | 0-2 | Leyton Orient |
| 3rd Round | Swindon Town | 0-0 | Barnsley |
| 3rd Round | Tottenham Hotspur | 5-2 | Watford |
| 3rd Round | 0-1 | Ipswich Town |
| 3rd Round | West Ham United | 1-1 | Swansea City |
| 3rd Round | 1-0 | Manchester City |
| 3rd Round | Wrexham | 4-3 | Scunthorpe United |
15th December 1998
| 2nd Round Replay | Brentford | 2-2 | Oldham Athletic |
| 2nd Round Replay | Bristol Rovers | 5-0 | Exeter City |
| 2nd Round Replay | Leyton Orient | 2-1 |
| 2nd Round Replay | Manchester City | 1-0 |
| 2nd Round Replay | Plymouth Argyle | 3-2 | Wycombe Wanderers |
| 2nd Round Replay | Rotherham United | 4-0 |
| 2nd Round Replay | 4-2 |
| 2nd Round Replay | Wigan Athletic | 0-0 | Notts. County |
6th December 1998
| 2nd Round | 0-0 | Leyton Orient |
5th December 1998
| 2nd Round | Cardiff City | 3-1 |
| 2nd Round | 0-0 |
| 2nd Round | Exeter City | 2-2 | Bristol Rovers |
| 2nd Round | Fulham | 4-2 | Hartlepool United |
| 2nd Round | Lincoln City | 4-1 | Stevenage |
| 2nd Round | Luton Town | 1-2 | Hull City |
| 2nd Round | Macclesfield Town | 4-1 | Cambridge United |
| 2nd Round | Mansfield Town | 1-2 |
| 2nd Round | Notts. County | 1-1 | Wigan Athletic |
| 2nd Round | Oldham Athletic | 1-1 | Brentford |
| 2nd Round | Preston North End | 2-0 | Walsall |
| 2nd Round | 0-0 | Rotherham United |
| 2nd Round | Scunthorpe United | 2-0 |
| 2nd Round | Swansea City | 1-0 | Stoke City |
| 2nd Round | 0-1 | AFC Bournemouth |
| 2nd Round | Wrexham | 2-1 |
| 2nd Round | Wycombe Wanderers | 1-1 | Plymouth Argyle |
| 2nd Round | 2-0 | Northampton Town |
4th December 1998
| 2nd Round | 1-1 | Manchester City |
1st December 1998
| 1st Round Replay | 0-0 | Plymouth Argyle |
| 1st Round Replay | Notts. County | 3-0 |
24th November 1998
| 1st Round Replay | Exeter City | 4-1 |
| 1st Round Replay | 0-2 | Fulham |
| 1st Round Replay | 2-0 |
| 1st Round Replay | Rotherham United | 3-1 |
| 1st Round Replay | 1-1 | Macclesfield Town |
| 1st Round Replay | 1-1 |
| 1st Round Replay | 2-1 |
23rd November 1998
| 1st Round Replay | Stevenage | 2-0 |
17th November 1998
| 1st Round | 3-2 | Burnley |
15th November 1998
| 1st Round | Boreham Wood | 2-3 | Luton Town |
| 1st Round | 1-1 | Rotherham United |
| 1st Round | Fulham | 1-1 |
| 1st Round | 0-0 | Notts. County |
14th November 1998
| 1st Round | 1-2 | AFC Bournemouth |
| 1st Round | 4-1 | Colchester United |
| 1st Round | Brentford | 5-0 |
| 1st Round | Bristol Rovers | 3-0 |
| 1st Round | Cardiff City | 6-0 |
| 1st Round | Cheltenham Town | 0-1 | Lincoln City |
| 1st Round | 0-1 |
| 1st Round | 2-2 |
| 1st Round | Hartlepool United | 2-1 | Carlisle United |
| 1st Round | 3-1 | Barnet |
| 1st Round | 1-0 | Burton Albion |
| 1st Round | Leyton Orient | 4-2 | Brighton & Hove Albion |
| 1st Round | Macclesfield Town | 2-2 |
| 1st Round | Mansfield Town | 2-1 |
| 1st Round | Northampton Town | 2-1 |
| 1st Round | Oldham Athletic | 2-0 |
| 1st Round | Plymouth Argyle | 0-0 |
| 1st Round | Preston North End | 3-0 |
| 1st Round | Reading | 0-1 | Stoke City |
| 1st Round | 1-1 | Stevenage |
| 1st Round | 1-0 | Shrewsbury Town |
| 1st Round | 0-2 | Hull City |
| 1st Round | 1-1 |
| 1st Round | 0-1 |
| 1st Round | 2-2 | Exeter City |
| 1st Round | 0-2 | Cambridge United |
| 1st Round | Walsall | 1-0 |
| 1st Round | Wigan Athletic | 4-3 | Blackpool |
| 1st Round | 0-1 | Scunthorpe United |
| 1st Round | 0-1 |
| 1st Round | Wrexham | 1-0 | Peterborough United |
| 1st Round | Wycombe Wanderers | 1-0 | Chesterfield |
| 1st Round | 2-2 |
13th November 1998
| 1st Round | Manchester City | 3-0 | FC Halifax Town |
| 1st Round | Swansea City | 3-0 | Millwall |