27th February 2000
| Final | Leicester City | 2-1 |
2nd February 2000
| Semi Final 2nd Leg | Leicester City | 1-0 | Aston Villa |
26th January 2000
| Semi Final 2nd Leg | 3-0 | Bolton Wanderers |
25th January 2000
| Semi Final 1st Leg | Aston Villa | 0-0 | Leicester City |
12th January 2000
| Quarter Final | Leicester City | 3-3 | Fulham |
| Semi Final 1st Leg | Bolton Wanderers | 0-1 |
11th January 2000
| Quarter Final | West Ham United | 1-3 | Aston Villa |
15th December 1999
| 4th Round | Leicester City | 0-0 | Leeds United |
14th December 1999
| Quarter Final | Bolton Wanderers | 2-1 |
| Quarter Final | 2-1 | Middlesbrough |
1st December 1999
| 4th Round | Aston Villa | 4-0 | Southampton |
| 4th Round | Fulham | 3-1 | Tottenham Hotspur |
30th November 1999
| 4th Round | Birmingham City | 2-3 | West Ham United |
| 4th Round | Bolton Wanderers | 1-0 | Sheffield Wednesday |
| 4th Round | Huddersfield Town | 1-2 |
| 4th Round | Middlesbrough | 2-2 | Arsenal |
| 4th Round | 4-0 | Barnsley |
13th October 1999
| 3rd Round | Aston Villa | 3-0 | Manchester United |
| 3rd Round | Chelsea | 0-1 | Huddersfield Town |
| 3rd Round | Derby County | 1-2 | Bolton Wanderers |
| 3rd Round | Leeds United | 1-0 | Blackburn Rovers |
| 3rd Round | Leicester City | 2-0 | Grimsby Town |
| 3rd Round | Middlesbrough | 1-0 | Watford |
| 3rd Round | Sheffield Wednesday | 4-1 | Nottingham Forest |
| 3rd Round | Southampton | 2-1 | Liverpool |
| 3rd Round | Tottenham Hotspur | 3-1 | Crewe Alexandra |
| 3rd Round | West Ham United | 2-0 | AFC Bournemouth |
12th October 1999
| 3rd Round | Arsenal | 2-1 | Preston North End |
| 3rd Round | Birmingham City | 2-0 | Newcastle United |
| 3rd Round | Bradford City | 2-3 | Barnsley |
| 3rd Round | 2-0 | Oxford United |
| 3rd Round | West Bromwich Albion | 1-2 | Fulham |
| 3rd Round | 3-2 | Sunderland |
22nd September 1999
| 2nd Round 2nd Leg | Blackburn Rovers | 3-1 | Portsmouth |
| 2nd Round 2nd Leg | Bristol City | 0-0 | Nottingham Forest |
| 2nd Round 2nd Leg | Coventry City | 3-1 |
| 2nd Round 2nd Leg | Derby County | 3-1 | Swansea City |
| 2nd Round 2nd Leg | Everton | 0-1 | Oxford United |
| 2nd Round 2nd Leg | Leicester City | 4-2 | Crystal Palace |
| 2nd Round 2nd Leg | Reading | 2-2 | Bradford City |
| 2nd Round 2nd Leg | Sheffield Wednesday | 3-1 | Stoke City |
21st September 1999
| 2nd Round 2nd Leg | Aston Villa | 5-0 |
| 2nd Round 2nd Leg | Bolton Wanderers | 2-0 |
| 2nd Round 2nd Leg | AFC Bournemouth | 0-0 | Charlton Athletic |
| 2nd Round 2nd Leg | Bristol Rovers | 0-1 | Birmingham City |
| 2nd Round 2nd Leg | Fulham | 2-0 | Norwich City |
| 2nd Round 2nd Leg | Ipswich Town | 1-1 | Crewe Alexandra |
| 2nd Round 2nd Leg | Leyton Orient | 1-0 | Grimsby Town |
| 2nd Round 2nd Leg | Liverpool | 4-2 | Hull City |
| 2nd Round 2nd Leg | Middlesbrough | 2-1 | Chesterfield |
| 2nd Round 2nd Leg | Notts. County | 2-2 | Huddersfield Town |
| 2nd Round 2nd Leg | Preston North End | 3-0 | Sheffield United |
| 2nd Round 2nd Leg | Southampton | 4-3 | Manchester City |
| 2nd Round 2nd Leg | 3-3 | Barnsley |
| 2nd Round 2nd Leg | Walsall | 0-5 | Sunderland |
| 2nd Round 2nd Leg | Wigan Athletic | 3-1 | Watford |
| 2nd Round 2nd Leg | 3-1 | Cardiff City |
| 2nd Round 2nd Leg | Wycombe Wanderers | 3-4 | West Bromwich Albion |
15th September 1999
| 2nd Round 1st Leg | Manchester City | 0-0 | Southampton |
| 2nd Round 1st Leg | Nottingham Forest | 2-1 | Bristol City |
14th September 1999
| 2nd Round 1st Leg | Barnsley | 1-1 |
| 2nd Round 1st Leg | Birmingham City | 2-0 | Bristol Rovers |
| 2nd Round 1st Leg | Bradford City | 1-1 | Reading |
| 2nd Round 1st Leg | Cardiff City | 1-1 |
| 2nd Round 1st Leg | Charlton Athletic | 0-0 | AFC Bournemouth |
| 2nd Round 1st Leg | 0-1 | Aston Villa |
| 2nd Round 1st Leg | Chesterfield | 0-0 | Middlesbrough |
| 2nd Round 1st Leg | Crewe Alexandra | 2-1 | Ipswich Town |
| 2nd Round 1st Leg | Crystal Palace | 3-3 | Leicester City |
| 2nd Round 1st Leg | 1-4 | Bolton Wanderers |
| 2nd Round 1st Leg | Grimsby Town | 4-1 | Leyton Orient |
| 2nd Round 1st Leg | Huddersfield Town | 2-1 | Notts. County |
| 2nd Round 1st Leg | Hull City | 1-5 | Liverpool |
| 2nd Round 1st Leg | Norwich City | 0-4 | Fulham |
| 2nd Round 1st Leg | Oxford United | 1-1 | Everton |
| 2nd Round 1st Leg | Portsmouth | 0-3 | Blackburn Rovers |
| 2nd Round 1st Leg | Sheffield United | 2-0 | Preston North End |
| 2nd Round 1st Leg | Stoke City | 0-0 | Sheffield Wednesday |
| 2nd Round 1st Leg | Sunderland | 3-2 | Walsall |
| 2nd Round 1st Leg | Swansea City | 0-0 | Derby County |
| 2nd Round 1st Leg | 5-1 | Coventry City |
| 2nd Round 1st Leg | Watford | 2-0 | Wigan Athletic |
| 2nd Round 1st Leg | West Bromwich Albion | 1-1 | Wycombe Wanderers |
25th August 1999
| 1st Round 2nd Leg | Bristol Rovers | 2-2 | Luton Town |
| 1st Round 2nd Leg | Queens Park Rangers | 1-2 | Cardiff City |
| 1st Round 2nd Leg | Stoke City | 3-0 | Macclesfield Town |
24th August 1999
| 1st Round 2nd Leg | Barnet | 3-2 | AFC Bournemouth |
| 1st Round 2nd Leg | Barnsley | 2-2 | Lincoln City |
| 1st Round 2nd Leg | Bolton Wanderers | 5-3 |
| 1st Round 2nd Leg | Bristol City | 2-1 | Cambridge United |
| 1st Round 2nd Leg | Burnley | 0-1 | Manchester City |
| 1st Round 2nd Leg | Cheltenham Town | 2-1 | Norwich City |
| 1st Round 2nd Leg | Chesterfield | 2-1 |
| 1st Round 2nd Leg | Crewe Alexandra | 1-0 | Hartlepool United |
| 1st Round 2nd Leg | Crystal Palace | 3-1 | Colchester United |
| 1st Round 2nd Leg | Exeter City | 1-2 | Birmingham City |
| 1st Round 2nd Leg | Fulham | 3-1 | Northampton Town |
| 1st Round 2nd Leg | 2-0 | Brighton & Hove Albion |
| 1st Round 2nd Leg | Grimsby Town | 6-0 | Carlisle United |
| 1st Round 2nd Leg | Huddersfield Town | 0-0 | Scunthorpe United |
| 1st Round 2nd Leg | Hull City | 2-0 | Rotherham United |
| 1st Round 2nd Leg | Ipswich Town | 2-0 | Brentford |
| 1st Round 2nd Leg | Leyton Orient | 1-1 | Swindon Town |
| 1st Round 2nd Leg | Mansfield Town | 1-0 | Nottingham Forest |
| 1st Round 2nd Leg | Millwall | 1-1 | Swansea City |
| 1st Round 2nd Leg | Notts. County | 2-0 |
| 1st Round 2nd Leg | Oldham Athletic | 1-1 |
| 1st Round 2nd Leg | Oxford United | 1-0 |
| 1st Round 2nd Leg | Peterborough United | 1-2 | Reading |
| 1st Round 2nd Leg | Plymouth Argyle | 1-4 | Walsall |
| 1st Round 2nd Leg | Port Vale | 4-4 |
| 1st Round 2nd Leg | Portsmouth | 3-0 |
| 1st Round 2nd Leg | Shrewsbury Town | 0-3 | Sheffield United |
| 1st Round 2nd Leg | 3-1 | Blackpool |
| 1st Round 2nd Leg | West Bromwich Albion | 5-1 | FC Halifax Town |
| 1st Round 2nd Leg | Wigan Athletic | 2-1 |
| 1st Round 2nd Leg | Wolverhampton Wanderers | 2-4 | Wycombe Wanderers |
| 1st Round 2nd Leg | Wrexham | 0-2 | Preston North End |
17th August 1999
| 1st Round 1st Leg | 0-0 | Portsmouth |
11th August 1999
| 1st Round 1st Leg | Brentford | 0-2 | Ipswich Town |
| 1st Round 1st Leg | Brighton & Hove Albion | 0-2 |
| 1st Round 1st Leg | Manchester City | 5-0 | Burnley |
| 1st Round 1st Leg | Nottingham Forest | 3-0 | Mansfield Town |
| 1st Round 1st Leg | Reading | 0-0 | Peterborough United |
| 1st Round 1st Leg | Swansea City | 2-0 | Millwall |
10th August 1999
| 1st Round 1st Leg | Birmingham City | 3-0 | Exeter City |
| 1st Round 1st Leg | Blackpool | 2-1 |
| 1st Round 1st Leg | AFC Bournemouth | 2-0 | Barnet |
| 1st Round 1st Leg | 1-0 | Notts. County |
| 1st Round 1st Leg | Cambridge United | 2-2 | Bristol City |
| 1st Round 1st Leg | Cardiff City | 1-2 | Queens Park Rangers |
| 1st Round 1st Leg | Carlisle United | 0-0 | Grimsby Town |
| 1st Round 1st Leg | 2-1 | Port Vale |
| 1st Round 1st Leg | Colchester United | 2-2 | Crystal Palace |
| 1st Round 1st Leg | 1-1 | Bolton Wanderers |
| 1st Round 1st Leg | FC Halifax Town | 0-0 | West Bromwich Albion |
| 1st Round 1st Leg | Hartlepool United | 3-3 | Crewe Alexandra |
| 1st Round 1st Leg | Lincoln City | 2-4 | Barnsley |
| 1st Round 1st Leg | Luton Town | 0-2 | Bristol Rovers |
| 1st Round 1st Leg | Macclesfield Town | 1-1 | Stoke City |
| 1st Round 1st Leg | Northampton Town | 1-2 | Fulham |
| 1st Round 1st Leg | Norwich City | 2-0 | Cheltenham Town |
| 1st Round 1st Leg | Preston North End | 1-0 | Wrexham |
| 1st Round 1st Leg | 1-2 | Chesterfield |
| 1st Round 1st Leg | Rotherham United | 0-1 | Hull City |
| 1st Round 1st Leg | Scunthorpe United | 0-2 | Huddersfield Town |
| 1st Round 1st Leg | Sheffield United | 3-0 | Shrewsbury Town |
| 1st Round 1st Leg | 0-2 | Oxford United |
| 1st Round 1st Leg | 2-0 | Oldham Athletic |
| 1st Round 1st Leg | Swindon Town | 0-1 | Leyton Orient |
| 1st Round 1st Leg | Walsall | 4-1 | Plymouth Argyle |
| 1st Round 1st Leg | Wycombe Wanderers | 0-1 | Wolverhampton Wanderers |
| 1st Round 1st Leg | 0-1 | Wigan Athletic |