20th May 2000
| Final | Chelsea | 1-0 | Aston Villa |
9th April 2000
| Semi Final | Chelsea | 2-1 | Newcastle United |
2nd April 2000
| Semi Final | Aston Villa | 0-0 | Bolton Wanderers |
20th February 2000
| 6th Round | Chelsea | 5-0 |
| 6th Round | Everton | 1-2 | Aston Villa |
| 6th Round | 2-3 | Newcastle United |
19th February 2000
| 6th Round | Bolton Wanderers | 1-0 | Charlton Athletic |
31st January 2000
| 5th Round | Blackburn Rovers | 1-2 | Newcastle United |
30th January 2000
| 5th Round | Aston Villa | 3-2 | Leeds United |
| 5th Round | Chelsea | 2-1 | Leicester City |
29th January 2000
| 5th Round | Cambridge United | 1-3 | Bolton Wanderers |
| 5th Round | Coventry City | 2-3 | Charlton Athletic |
| 5th Round | Everton | 2-0 | Preston North End |
| 5th Round | Fulham | 1-2 |
| 5th Round | 3-1 | Sheffield Wednesday |
19th January 2000
| 4th Round | Chelsea | 2-0 | Nottingham Forest |
| 4th Round Replay | Leicester City | 0-0 | Arsenal |
18th January 2000
| 4th Round Replay | Wolverhampton Wanderers | 0-0 | Sheffield Wednesday |
11th January 2000
| 4th Round | 3-1 | Bradford City |
10th January 2000
| 4th Round | Liverpool | 0-1 | Blackburn Rovers |
9th January 2000
| 4th Round | Arsenal | 0-0 | Leicester City |
| 4th Round | Manchester City | 2-5 | Leeds United |
8th January 2000
| 3rd Round Replay | 2-1 | Walsall |
| 3rd Round Replay | Oxford United | 1-3 | Nottingham Forest |
| 4th Round | Aston Villa | 1-0 | Southampton |
| 4th Round | Charlton Athletic | 1-0 | Queens Park Rangers |
| 4th Round | Coventry City | 3-0 | Burnley |
| 4th Round | Everton | 2-0 | Birmingham City |
| 4th Round | Fulham | 3-0 |
| 4th Round | Grimsby Town | 0-2 | Bolton Wanderers |
| 4th Round | Newcastle United | 4-1 | Sheffield United |
| 4th Round | Plymouth Argyle | 0-3 | Preston North End |
| 4th Round | Sheffield Wednesday | 1-1 | Wolverhampton Wanderers |
| 4th Round | 1-0 | Sunderland |
| 4th Round | Wrexham | 1-2 | Cambridge United |
22nd December 1999
| 3rd Round Replay | Blackburn Rovers | 2-0 | West Bromwich Albion |
| 3rd Round Replay | Leicester City | 2-1 |
| 3rd Round Replay | Newcastle United | 6-1 | Tottenham Hotspur |
21st December 1999
| 3rd Round | Bolton Wanderers | 1-0 | Cardiff City |
| 3rd Round Replay | Everton | 1-0 | Exeter City |
| 3rd Round Replay | Luton Town | 0-3 | Fulham |
| 3rd Round Replay | Plymouth Argyle | 1-0 | Reading |
| 3rd Round Replay | 1-1 | Sheffield United |
| 3rd Round Replay | 2-3 | Queens Park Rangers |
13th December 1999
| 3rd Round | Arsenal | 3-1 | Blackpool |
| 3rd Round | Ipswich Town | 0-1 | Southampton |
12th December 1999
| 3rd Round | 1-4 | Manchester City |
| 3rd Round | Huddersfield Town | 0-2 | Liverpool |
| 3rd Round | Leeds United | 2-0 | Port Vale |
| 3rd Round | Sheffield United | 1-1 |
| 3rd Round | Tottenham Hotspur | 1-1 | Newcastle United |
11th December 1999
| 3rd Round | Aston Villa | 2-1 |
| 3rd Round | Charlton Athletic | 2-1 | Swindon Town |
| 3rd Round | Crewe Alexandra | 1-2 | Bradford City |
| 3rd Round | Derby County | 0-1 | Burnley |
| 3rd Round | Exeter City | 0-0 | Everton |
| 3rd Round | Fulham | 2-2 | Luton Town |
| 3rd Round | Grimsby Town | 3-2 |
| 3rd Round | 0-0 | Leicester City |
| 3rd Round | Hull City | 1-6 | Chelsea |
| 3rd Round | Norwich City | 1-3 | Coventry City |
| 3rd Round | Preston North End | 2-1 | Oldham Athletic |
| 3rd Round | Queens Park Rangers | 1-1 |
| 3rd Round | Reading | 1-1 | Plymouth Argyle |
| 3rd Round | Sheffield Wednesday | 1-0 | Bristol City |
| 3rd Round | Sunderland | 1-0 | Portsmouth |
| 3rd Round | 1-0 | West Ham United |
| 3rd Round | West Bromwich Albion | 2-2 | Blackburn Rovers |
| 3rd Round | Watford | 0-1 | Birmingham City |
| 3rd Round | Walsall | 1-1 |
| 3rd Round | Wigan Athletic | 0-1 | Wolverhampton Wanderers |
| 3rd Round | 1-0 | Barnsley |
| 3rd Round | Wrexham | 2-1 | Middlesbrough |
10th December 1999
| 3rd Round | Cambridge United | 2-0 | Crystal Palace |
| 3rd Round | Nottingham Forest | 1-1 | Oxford United |
30th November 1999
| 2nd Round Replay | Brighton & Hove Albion | 1-2 | Plymouth Argyle |
| 2nd Round Replay | Cardiff City | 1-0 |
| 2nd Round Replay | 0-3 | Preston North End |
| 2nd Round Replay | FC Halifax Town | 0-1 | Reading |
| 2nd Round Replay | Hull City | 3-2 |
| 2nd Round Replay | Lincoln City | 0-1 | Luton Town |
| 2nd Round Replay | Oxford United | 2-1 | Shrewsbury Town |
| 2nd Round Replay | 3-0 |
| 2nd Round Replay | Wigan Athletic | 2-1 | Wycombe Wanderers |
21st November 1999
| 2nd Round | Forest Green Rovers | 0-3 |
| 2nd Round | 1-0 | Hartlepool United |
20th November 1999
| 2nd Round | Blackpool | 2-0 |
| 2nd Round | AFC Bournemouth | 0-2 | Bristol City |
| 2nd Round | Burnley | 2-0 | Rotherham United |
| 2nd Round | 0-0 | Cardiff City |
| 2nd Round | Cambridge United | 1-0 |
| 2nd Round | Exeter City | 2-0 | Aldershot Town |
| 2nd Round | 3-1 |
| 2nd Round | 2-2 | Hull City |
| 2nd Round | 1-1 |
| 2nd Round | Oldham Athletic | 1-0 | Swansea City |
| 2nd Round | Plymouth Argyle | 0-0 | Brighton & Hove Albion |
| 2nd Round | Preston North End | 0-0 |
| 2nd Round | Reading | 1-1 | FC Halifax Town |
| 2nd Round | Shrewsbury Town | 2-2 | Oxford United |
| 2nd Round | 1-2 |
| 2nd Round | Wrexham | 2-1 |
| 2nd Round | Wycombe Wanderers | 2-2 | Wigan Athletic |
19th November 1999
| 2nd Round | Luton Town | 2-2 | Lincoln City |
16th November 1999
| 1st Round Replay | 0-1 | Wycombe Wanderers |
10th November 1999
| 1st Round Replay | 0-2 | Wrexham |
9th November 1999
| 1st Round Replay | AFC Bournemouth | 4-2 | Notts. County |
| 1st Round Replay | Brighton & Hove Albion | 3-0 | Peterborough United |
| 1st Round Replay | 2-1 |
| 1st Round Replay | Cardiff City | 3-1 | Leyton Orient |
| 1st Round Replay | 3-1 |
| 1st Round Replay | 3-2 | Cheltenham Town |
| 1st Round Replay | Hull City | 4-0 | Macclesfield Town |
| 1st Round Replay | Plymouth Argyle | 2-1 | Brentford |
| 1st Round Replay | 3-0 | Burton Albion |
| 1st Round Replay | 3-1 |
8th November 1999
| 1st Round Replay | 1-2 | Aldershot Town |
2nd November 1999
| 1st Round | 2-2 |
31st October 1999
| 1st Round | Barnet | 0-1 | Burnley |
| 1st Round | Bristol Rovers | 0-1 | Preston North End |
| 1st Round | Hartlepool United | 1-0 | Millwall |
30th October 1999
| 1st Round | Aldershot Town | 1-1 |
| 1st Round | 0-2 |
| 1st Round | Blackpool | 2-0 | Stoke City |
| 1st Round | Brentford | 2-2 | Plymouth Argyle |
| 1st Round | Bristol City | 3-2 | Mansfield Town |
| 1st Round | Burton Albion | 0-0 |
| 1st Round | 0-2 | Wigan Athletic |
| 1st Round | Cambridge United | 1-0 | Gateshead |
| 1st Round | Cheltenham Town | 1-1 |
| 1st Round | Chesterfield | 1-2 |
| 1st Round | 2-1 |
| 1st Round | 0-2 | FC Halifax Town |
| 1st Round | Exeter City | 2-1 |
| 1st Round | Forest Green Rovers | 6-0 |
| 1st Round | 2-1 |
| 1st Round | 1-0 |
| 1st Round | 2-1 | Carlisle United |
| 1st Round | Leyton Orient | 1-1 | Cardiff City |
| 1st Round | Lincoln City | 1-0 |
| 1st Round | Luton Town | 4-2 |
| 1st Round | Macclesfield Town | 0-0 | Hull City |
| 1st Round | Notts. County | 1-1 | AFC Bournemouth |
| 1st Round | Oldham Athletic | 4-0 |
| 1st Round | Oxford United | 3-2 | Morecambe |
| 1st Round | Peterborough United | 1-1 | Brighton & Hove Albion |
| 1st Round | Reading | 4-2 |
| 1st Round | Rotherham United | 3-0 |
| 1st Round | Shrewsbury Town | 2-1 | Northampton Town |
| 1st Round | 0-2 |
| 1st Round | Swansea City | 2-1 | Colchester United |
| 1st Round | 2-2 |
| 1st Round | 1-0 |
| 1st Round | 0-0 |
| 1st Round | Wrexham | 1-1 |
| 1st Round | Wycombe Wanderers | 1-1 |
29th October 1999
| 1st Round | 2-0 | Scunthorpe United |