21st March 1999
| Final | Leicester City | 0-1 | Tottenham Hotspur |
17th February 1999
| Semi Final 2nd Leg | Leicester City | 1-1 | Sunderland |
16th February 1999
| Semi Final 2nd Leg | 0-1 | Tottenham Hotspur |
27th January 1999
| Semi Final 1st Leg | Tottenham Hotspur | 0-0 |
26th January 1999
| Semi Final 1st Leg | Sunderland | 1-2 | Leicester City |
2nd December 1998
| Quarter Final | Leicester City | 1-0 | Blackburn Rovers |
| Quarter Final | Tottenham Hotspur | 3-1 | Manchester United |
1st December 1998
| Quarter Final | Sunderland | 3-0 | Luton Town |
| Quarter Final | 2-1 | Chelsea |
11th November 1998
| 4th Round | Arsenal | 0-5 | Chelsea |
| 4th Round | Everton | 1-1 | Sunderland |
| 4th Round | Leicester City | 2-1 | Leeds United |
| 4th Round | Manchester United | 2-1 | Nottingham Forest |
| 4th Round | Newcastle United | 1-1 | Blackburn Rovers |
10th November 1998
| 4th Round | Bolton Wanderers | 1-2 |
| 4th Round | Liverpool | 1-3 | Tottenham Hotspur |
| 4th Round | Luton Town | 1-0 | Barnsley |
28th October 1998
| 3rd Round | Birmingham City | 1-2 |
| 3rd Round | Chelsea | 4-1 | Aston Villa |
| 3rd Round | Crewe Alexandra | 0-1 | Blackburn Rovers |
| 3rd Round | Derby County | 1-2 | Arsenal |
| 3rd Round | Leeds United | 1-0 | Bradford City |
| 3rd Round | Manchester United | 2-0 |
| 3rd Round | Middlesbrough | 2-3 | Everton |
27th October 1998
| 3rd Round | Barnsley | 2-1 | AFC Bournemouth |
| 3rd Round | Charlton Athletic | 1-2 | Leicester City |
| 3rd Round | Liverpool | 3-1 | Fulham |
| 3rd Round | Luton Town | 2-0 | Coventry City |
| 3rd Round | Northampton Town | 1-3 | Tottenham Hotspur |
| 3rd Round | Norwich City | 1-1 | Bolton Wanderers |
| 3rd Round | Nottingham Forest | 3-3 | Cambridge United |
| 3rd Round | Sunderland | 2-1 | Grimsby Town |
| 3rd Round | 0-1 | Newcastle United |
23rd September 1998
| 2nd Round 2nd Leg | Crystal Palace | 2-1 |
| 2nd Round 2nd Leg | Everton | 2-1 | Huddersfield Town |
| 2nd Round 2nd Leg | Manchester City | 0-1 | Derby County |
| 2nd Round 2nd Leg | Reading | 1-1 | Barnsley |
| 2nd Round 2nd Leg | Southampton | 0-1 | Fulham |
| 2nd Round 2nd Leg | Tottenham Hotspur | 3-2 | Brentford |
22nd September 1998
| 2nd Round 2nd Leg | Birmingham City | 6-0 | Macclesfield Town |
| 2nd Round 2nd Leg | Bradford City | 3-1 | FC Halifax Town |
| 2nd Round 2nd Leg | Cambridge United | 1-1 | Sheffield Wednesday |
| 2nd Round 2nd Leg | Charlton Athletic | 1-0 | Queens Park Rangers |
| 2nd Round 2nd Leg | 0-1 | Sunderland |
| 2nd Round 2nd Leg | Chesterfield | 1-3 | Leicester City |
| 2nd Round 2nd Leg | Crewe Alexandra | 2-0 | Bristol City |
| 2nd Round 2nd Leg | Grimsby Town | 2-0 | Sheffield United |
| 2nd Round 2nd Leg | Hull City | 2-3 | Bolton Wanderers |
| 2nd Round 2nd Leg | Luton Town | 4-2 | Ipswich Town |
| 2nd Round 2nd Leg | Nottingham Forest | 0-0 | Leyton Orient |
| 2nd Round 2nd Leg | 0-4 | Coventry City |
| 2nd Round 2nd Leg | 3-1 | Blackpool |
| 2nd Round 2nd Leg | West Ham United | 1-0 | Northampton Town |
| 2nd Round 2nd Leg | Wigan Athletic | 2-3 | Norwich City |
| 2nd Round 2nd Leg | 4-1 | Portsmouth |
| 2nd Round 2nd Leg | Wolverhampton Wanderers | 1-2 | AFC Bournemouth |
| 2nd Round 2nd Leg | Wycombe Wanderers | 1-1 | Middlesbrough |
16th September 1998
| 2nd Round 1st Leg | Bristol City | 1-1 | Crewe Alexandra |
| 2nd Round 1st Leg | Coventry City | 1-0 |
| 2nd Round 1st Leg | Derby County | 1-1 | Manchester City |
| 2nd Round 1st Leg | Leicester City | 3-0 | Chesterfield |
| 2nd Round 1st Leg | Middlesbrough | 2-0 | Wycombe Wanderers |
| 2nd Round 1st Leg | Norwich City | 1-0 | Wigan Athletic |
| 2nd Round 1st Leg | Queens Park Rangers | 0-2 | Charlton Athletic |
| 2nd Round 1st Leg | Sheffield Wednesday | 0-1 | Cambridge United |
15th September 1998
| 2nd Round 1st Leg | Barnsley | 3-0 | Reading |
| 2nd Round 1st Leg | Blackpool | 2-1 |
| 2nd Round 1st Leg | Bolton Wanderers | 3-1 | Hull City |
| 2nd Round 1st Leg | AFC Bournemouth | 1-1 | Wolverhampton Wanderers |
| 2nd Round 1st Leg | Brentford | 2-3 | Tottenham Hotspur |
| 2nd Round 1st Leg | 3-0 | Crystal Palace |
| 2nd Round 1st Leg | Fulham | 1-1 | Southampton |
| 2nd Round 1st Leg | FC Halifax Town | 1-2 | Bradford City |
| 2nd Round 1st Leg | Huddersfield Town | 1-1 | Everton |
| 2nd Round 1st Leg | Ipswich Town | 2-1 | Luton Town |
| 2nd Round 1st Leg | Leyton Orient | 1-5 | Nottingham Forest |
| 2nd Round 1st Leg | Macclesfield Town | 0-3 | Birmingham City |
| 2nd Round 1st Leg | Northampton Town | 2-0 | West Ham United |
| 2nd Round 1st Leg | Portsmouth | 2-1 |
| 2nd Round 1st Leg | Sheffield United | 2-1 | Grimsby Town |
| 2nd Round 1st Leg | Sunderland | 3-0 |
26th August 1998
| 1st Round 2nd Leg | Queens Park Rangers | 3-1 | Walsall |
| 1st Round 2nd Leg | Reading | 2-0 | Peterborough United |
25th August 1998
| 1st Round 2nd Leg | Crystal Palace | 2-1 |
19th August 1998
| 1st Round 2nd Leg | Brighton & Hove Albion | 1-1 | Northampton Town |
| 1st Round 2nd Leg | Manchester City | 7-1 | Notts. County |
| 1st Round 2nd Leg | Stoke City | 1-0 | Macclesfield Town |
18th August 1998
| 1st Round 2nd Leg | Barnsley | 3-0 |
| 1st Round 2nd Leg | Brentford | 3-0 | West Bromwich Albion |
| 1st Round 2nd Leg | Bristol Rovers | 1-2 | Leyton Orient |
| 1st Round 2nd Leg | Burnley | 1-4 |
| 1st Round 2nd Leg | Cardiff City | 1-2 | Fulham |
| 1st Round 2nd Leg | Carlisle United | 0-1 |
| 1st Round 2nd Leg | 2-2 | Port Vale |
| 1st Round 2nd Leg | Chesterfield | 2-0 | Rotherham United |
| 1st Round 2nd Leg | Colchester United | 3-2 | AFC Bournemouth |
| 1st Round 2nd Leg | Crewe Alexandra | 2-0 | Oldham Athletic |
| 1st Round 2nd Leg | 2-2 | Sheffield United |
| 1st Round 2nd Leg | 0-1 |
| 1st Round 2nd Leg | FC Halifax Town | 0-2 | Wrexham |
| 1st Round 2nd Leg | Hartlepool United | 0-3 | Bolton Wanderers |
| 1st Round 2nd Leg | Hull City | 0-0 |
| 1st Round 2nd Leg | Ipswich Town | 5-1 | Exeter City |
| 1st Round 2nd Leg | Lincoln City | 0-1 | Bradford City |
| 1st Round 2nd Leg | Mansfield Town | 1-1 | Huddersfield Town |
| 1st Round 2nd Leg | Millwall | 1-1 | Birmingham City |
| 1st Round 2nd Leg | Norwich City | 1-0 | Swansea City |
| 1st Round 2nd Leg | Oxford United | 1-3 | Luton Town |
| 1st Round 2nd Leg | Portsmouth | 3-2 | Plymouth Argyle |
| 1st Round 2nd Leg | Preston North End | 0-0 | Grimsby Town |
| 1st Round 2nd Leg | 0-1 | Wigan Athletic |
| 1st Round 2nd Leg | Scunthorpe United | 1-1 | Blackpool |
| 1st Round 2nd Leg | Shrewsbury Town | 4-3 | Bristol City |
| 1st Round 2nd Leg | Sunderland | 2-1 |
| 1st Round 2nd Leg | Watford | 1-1 | Cambridge United |
| 1st Round 2nd Leg | Wolverhampton Wanderers | 5-0 | Barnet |
| 1st Round 2nd Leg | Wycombe Wanderers | 2-0 | Swindon Town |
12th August 1998
| 1st Round 1st Leg | Grimsby Town | 0-0 | Preston North End |
| 1st Round 1st Leg | 0-1 | Barnsley |
| 1st Round 1st Leg | Swindon Town | 2-1 | Wycombe Wanderers |
11th August 1998
| 1st Round 1st Leg | Barnet | 2-1 | Wolverhampton Wanderers |
| 1st Round 1st Leg | Birmingham City | 2-0 | Millwall |
| 1st Round 1st Leg | Blackpool | 1-0 | Scunthorpe United |
| 1st Round 1st Leg | Bolton Wanderers | 1-0 | Hartlepool United |
| 1st Round 1st Leg | AFC Bournemouth | 2-0 | Colchester United |
| 1st Round 1st Leg | Bradford City | 1-1 | Lincoln City |
| 1st Round 1st Leg | Bristol City | 4-0 | Shrewsbury Town |
| 1st Round 1st Leg | 1-1 | Burnley |
| 1st Round 1st Leg | Cambridge United | 1-0 | Watford |
| 1st Round 1st Leg | Exeter City | 1-1 | Ipswich Town |
| 1st Round 1st Leg | Fulham | 2-1 | Cardiff City |
| 1st Round 1st Leg | Huddersfield Town | 3-2 | Mansfield Town |
| 1st Round 1st Leg | Leyton Orient | 1-1 | Bristol Rovers |
| 1st Round 1st Leg | Luton Town | 2-3 | Oxford United |
| 1st Round 1st Leg | Macclesfield Town | 3-1 | Stoke City |
| 1st Round 1st Leg | Northampton Town | 2-1 | Brighton & Hove Albion |
| 1st Round 1st Leg | Notts. County | 0-2 | Manchester City |
| 1st Round 1st Leg | Oldham Athletic | 3-2 | Crewe Alexandra |
| 1st Round 1st Leg | Peterborough United | 1-1 | Reading |
| 1st Round 1st Leg | Plymouth Argyle | 1-3 | Portsmouth |
| 1st Round 1st Leg | Port Vale | 1-2 |
| 1st Round 1st Leg | Rotherham United | 0-1 | Chesterfield |
| 1st Round 1st Leg | Sheffield United | 3-1 |
| 1st Round 1st Leg | 1-0 |
| 1st Round 1st Leg | 2-2 | Hull City |
| 1st Round 1st Leg | Swansea City | 1-1 | Norwich City |
| 1st Round 1st Leg | 1-1 | Crystal Palace |
| 1st Round 1st Leg | 3-0 | Carlisle United |
| 1st Round 1st Leg | Walsall | 0-0 | Queens Park Rangers |
| 1st Round 1st Leg | West Bromwich Albion | 2-1 | Brentford |
| 1st Round 1st Leg | Wigan Athletic | 1-0 |
| 1st Round 1st Leg | Wrexham | 0-2 | FC Halifax Town |
| 1st Round 1st Leg | 0-2 | Sunderland |