29th April 1990
| Final | Nottingham Forest | 1-0 | Oldham Athletic |
7th March 1990
| Semi Final 2nd Leg | West Ham United | 3-0 | Oldham Athletic |
25th February 1990
| Semi Final 2nd Leg | Coventry City | 0-0 | Nottingham Forest |
14th February 1990
| Semi Final 1st Leg | Oldham Athletic | 6-0 | West Ham United |
11th February 1990
| Semi Final 1st Leg | Nottingham Forest | 2-1 | Coventry City |
31st January 1990
| Quarter Final Replay | Oldham Athletic | 2-0 | Southampton |
| Quarter Final 2nd Replay | West Ham United | 2-1 | Derby County |
24th January 1990
| Quarter Final | Southampton | 2-2 | Oldham Athletic |
| Quarter Final Replay | Coventry City | 5-0 | Sunderland |
| Quarter Final Replay | Derby County | 0-0 | West Ham United |
| Quarter Final Replay | Tottenham Hotspur | 2-3 | Nottingham Forest |
17th January 1990
| Quarter Final | Nottingham Forest | 2-2 | Tottenham Hotspur |
| Quarter Final | Sunderland | 0-0 | Coventry City |
| Quarter Final | West Ham United | 1-1 | Derby County |
16th January 1990
| 4th Round Replay | Southampton | 4-2 | Swindon Town |
5th December 1989
| 4th Round Replay | Sunderland | 5-2 | Exeter City |
29th November 1989
| 4th Round | Exeter City | 2-2 | Sunderland |
| 4th Round | Swindon Town | 0-0 | Southampton |
| 4th Round Replay | Tottenham Hotspur | 4-0 |
22nd November 1989
| 4th Round | Derby County | 2-0 | West Bromwich Albion |
| 4th Round | Manchester City | 0-1 | Coventry City |
| 4th Round | Nottingham Forest | 1-0 | Everton |
| 4th Round | Oldham Athletic | 3-1 | Arsenal |
| 4th Round | 2-2 | Tottenham Hotspur |
| 4th Round | West Ham United | 1-0 |
21st November 1989
| 3rd Round Replay | Swindon Town | 2-1 | Bolton Wanderers |
14th November 1989
| 3rd Round 2nd Replay | Bolton Wanderers | 1-1 | Swindon Town |
8th November 1989
| 3rd Round Replay | West Ham United | 1-0 | Aston Villa |
| 3rd Round Replay | 1-0 | Middlesbrough |
7th November 1989
| 3rd Round Replay | Bolton Wanderers | 1-1 | Swindon Town |
| 3rd Round Replay | AFC Bournemouth | 0-1 | Sunderland |
1st November 1989
| 3rd Round Replay | Nottingham Forest | 5-0 | Crystal Palace |
25th October 1989
| 3rd Round | Arsenal | 1-0 | Liverpool |
| 3rd Round | Aston Villa | 0-0 | West Ham United |
| 3rd Round | Derby County | 2-1 | Sheffield Wednesday |
| 3rd Round | Exeter City | 3-0 | Blackpool |
| 3rd Round | Manchester City | 3-1 | Norwich City |
| 3rd Round | Manchester United | 0-3 | Tottenham Hotspur |
| 3rd Round | Middlesbrough | 1-1 |
| 3rd Round | Newcastle United | 0-1 | West Bromwich Albion |
| 3rd Round | Oldham Athletic | 7-0 |
| 3rd Round | Queens Park Rangers | 1-2 | Coventry City |
24th October 1989
| 3rd Round | Crystal Palace | 0-0 | Nottingham Forest |
| 3rd Round | Everton | 3-0 | Luton Town |
| 3rd Round | Southampton | 1-0 | Charlton Athletic |
| 3rd Round | Sunderland | 1-1 | AFC Bournemouth |
| 3rd Round | Swindon Town | 3-3 | Bolton Wanderers |
23rd October 1989
| 3rd Round | 3-2 | Millwall |
4th October 1989
| 2nd Round 2nd Leg | Bradford City | 3-5 | West Bromwich Albion |
| 2nd Round 2nd Leg | Coventry City | 3-0 | Grimsby Town |
| 2nd Round 2nd Leg | Derby County | 5-0 | Cambridge United |
| 2nd Round 2nd Leg | 0-1 | Charlton Athletic |
| 2nd Round 2nd Leg | Leicester City | 2-3 | Crystal Palace |
| 2nd Round 2nd Leg | Manchester City | 4-1 | Brentford |
| 2nd Round 2nd Leg | Newcastle United | 4-0 | Reading |
| 2nd Round 2nd Leg | 3-2 | Chelsea |
| 2nd Round 2nd Leg | 3-2 | Tottenham Hotspur |
| 2nd Round 2nd Leg | West Ham United | 1-1 | Birmingham City |
| 2nd Round 2nd Leg | Wigan Athletic | 0-3 | Liverpool |
| 2nd Round 2nd Leg | 3-0 | Port Vale |
| 2nd Round 2nd Leg | Wolverhampton Wanderers | 1-1 | Aston Villa |
3rd October 1989
| 2nd Round 2nd Leg | Aldershot Town | 0-8 | Sheffield Wednesday |
| 2nd Round 2nd Leg | Blackburn Rovers | 2-1 | Exeter City |
| 2nd Round 2nd Leg | Blackpool | 1-1 | Barnsley |
| 2nd Round 2nd Leg | AFC Bournemouth | 0-0 | Crewe Alexandra |
| 2nd Round 2nd Leg | Everton | 2-2 | Leyton Orient |
| 2nd Round 2nd Leg | Fulham | 0-3 | Sunderland |
| 2nd Round 2nd Leg | FC Halifax Town | 0-1 | Middlesbrough |
| 2nd Round 2nd Leg | Huddersfield Town | 3-3 | Nottingham Forest |
| 2nd Round 2nd Leg | Leeds United | 1-2 | Oldham Athletic |
| 2nd Round 2nd Leg | Luton Town | 7-2 | Mansfield Town |
| 2nd Round 2nd Leg | Manchester United | 0-0 | Portsmouth |
| 2nd Round 2nd Leg | Millwall | 2-0 | Stoke City |
| 2nd Round 2nd Leg | Plymouth Argyle | 1-6 | Arsenal |
| 2nd Round 2nd Leg | Rotherham United | 0-2 | Norwich City |
| 2nd Round 2nd Leg | Southampton | 2-0 |
| 2nd Round 2nd Leg | Swindon Town | 3-1 | Shrewsbury Town |
| 2nd Round 2nd Leg | 1-0 | Ipswich Town |
| 2nd Round 2nd Leg | Watford | 1-1 | Bolton Wanderers |
2nd October 1989
| 2nd Round 2nd Leg | 0-0 | Queens Park Rangers |
20th September 1989
| 2nd Round 1st Leg | Aston Villa | 2-1 | Wolverhampton Wanderers |
| 2nd Round 1st Leg | Charlton Athletic | 3-1 |
| 2nd Round 1st Leg | Exeter City | 3-0 | Blackburn Rovers |
| 2nd Round 1st Leg | Middlesbrough | 4-0 | FC Halifax Town |
| 2nd Round 1st Leg | Norwich City | 1-1 | Rotherham United |
| 2nd Round 1st Leg | Nottingham Forest | 1-1 | Huddersfield Town |
| 2nd Round 1st Leg | Portsmouth | 2-3 | Manchester United |
| 2nd Round 1st Leg | Queens Park Rangers | 2-1 |
| 2nd Round 1st Leg | Sheffield Wednesday | 0-0 | Aldershot Town |
| 2nd Round 1st Leg | Tottenham Hotspur | 1-0 |
| 2nd Round 1st Leg | West Bromwich Albion | 1-3 | Bradford City |
| 2nd Round 1st Leg | 0-1 | Southampton |
19th September 1989
| 2nd Round 1st Leg | Arsenal | 2-0 | Plymouth Argyle |
| 2nd Round 1st Leg | Barnsley | 1-1 | Blackpool |
| 2nd Round 1st Leg | Birmingham City | 1-2 | West Ham United |
| 2nd Round 1st Leg | Bolton Wanderers | 2-1 | Watford |
| 2nd Round 1st Leg | Brentford | 2-1 | Manchester City |
| 2nd Round 1st Leg | Cambridge United | 2-1 | Derby County |
| 2nd Round 1st Leg | Chelsea | 1-1 |
| 2nd Round 1st Leg | Crewe Alexandra | 0-1 | AFC Bournemouth |
| 2nd Round 1st Leg | Crystal Palace | 1-2 | Leicester City |
| 2nd Round 1st Leg | Grimsby Town | 3-1 | Coventry City |
| 2nd Round 1st Leg | Ipswich Town | 0-1 |
| 2nd Round 1st Leg | Leyton Orient | 0-2 | Everton |
| 2nd Round 1st Leg | Liverpool | 5-2 | Wigan Athletic |
| 2nd Round 1st Leg | Mansfield Town | 3-4 | Luton Town |
| 2nd Round 1st Leg | Oldham Athletic | 2-1 | Leeds United |
| 2nd Round 1st Leg | Reading | 3-1 | Newcastle United |
| 2nd Round 1st Leg | Shrewsbury Town | 0-3 | Swindon Town |
| 2nd Round 1st Leg | Stoke City | 1-0 | Millwall |
| 2nd Round 1st Leg | Sunderland | 1-1 | Fulham |
18th September 1989
| 2nd Round 1st Leg | Port Vale | 1-2 |
5th September 1989
| 1st Round 2nd Leg | Northampton Town | 0-2 | Mansfield Town |
30th August 1989
| 1st Round 2nd Leg | 3-0 |
| 1st Round 2nd Leg | Lincoln City | 0-2 | Wolverhampton Wanderers |
| 1st Round 2nd Leg | Maidstone United | 0-1 | Cambridge United |
| 1st Round 2nd Leg | Oxford United | 3-5 | Fulham |
29th August 1989
| 1st Round 2nd Leg | Aldershot Town | 6-2 | Peterborough United |
| 1st Round 2nd Leg | Bolton Wanderers | 5-1 |
| 1st Round 2nd Leg | Brentford | 1-1 | Brighton & Hove Albion |
| 1st Round 2nd Leg | Burnley | 0-1 | Blackpool |
| 1st Round 2nd Leg | 1-1 |
| 1st Round 2nd Leg | Carlisle United | 1-0 | FC Halifax Town |
| 1st Round 2nd Leg | 0-2 | Crewe Alexandra |
| 1st Round 2nd Leg | Chesterfield | 1-1 | Birmingham City |
| 1st Round 2nd Leg | 1-2 | Huddersfield Town |
| 1st Round 2nd Leg | Grimsby Town | 2-0 | Hull City |
| 1st Round 2nd Leg | Leyton Orient | 3-0 |
| 1st Round 2nd Leg | Notts. County | 3-1 | Shrewsbury Town |
| 1st Round 2nd Leg | Plymouth Argyle | 0-2 | Cardiff City |
| 1st Round 2nd Leg | Portsmouth | 2-0 | Bristol Rovers |
| 1st Round 2nd Leg | Reading | 2-2 | Bristol City |
| 1st Round 2nd Leg | Rotherham United | 1-0 | Sheffield United |
| 1st Round 2nd Leg | Scunthorpe United | 1-1 |
| 1st Round 2nd Leg | 2-1 | Colchester United |
| 1st Round 2nd Leg | Swansea City | 1-1 | Exeter City |
| 1st Round 2nd Leg | 3-1 | Preston North End |
| 1st Round 2nd Leg | Wigan Athletic | 5-0 | Wrexham |
| 1st Round 2nd Leg | 4-1 | Hartlepool United |
28th August 1989
| 1st Round 2nd Leg | Port Vale | 1-0 | Walsall |
23rd August 1989
| 1st Round 1st Leg | Brighton & Hove Albion | 0-3 | Brentford |
| 1st Round 1st Leg | Bristol Rovers | 1-0 | Portsmouth |
| 1st Round 1st Leg | Exeter City | 3-0 | Swansea City |
| 1st Round 1st Leg | Fulham | 0-1 | Oxford United |
| 1st Round 1st Leg | Hartlepool United | 3-3 |
| 1st Round 1st Leg | Peterborough United | 2-0 | Aldershot Town |
| 1st Round 1st Leg | 2-0 | Scunthorpe United |
22nd August 1989
| 1st Round 1st Leg | Birmingham City | 2-1 | Chesterfield |
| 1st Round 1st Leg | Blackpool | 2-2 | Burnley |
| 1st Round 1st Leg | Bristol City | 2-3 | Reading |
| 1st Round 1st Leg | Cambridge United | 3-1 | Maidstone United |
| 1st Round 1st Leg | Cardiff City | 0-3 | Plymouth Argyle |
| 1st Round 1st Leg | Colchester United | 3-4 |
| 1st Round 1st Leg | Crewe Alexandra | 4-0 |
| 1st Round 1st Leg | 1-4 | Leyton Orient |
| 1st Round 1st Leg | FC Halifax Town | 3-1 | Carlisle United |
| 1st Round 1st Leg | Huddersfield Town | 1-1 |
| 1st Round 1st Leg | Hull City | 1-0 | Grimsby Town |
| 1st Round 1st Leg | Mansfield Town | 1-1 | Northampton Town |
| 1st Round 1st Leg | Preston North End | 3-4 |
| 1st Round 1st Leg | 2-1 | Bolton Wanderers |
| 1st Round 1st Leg | Sheffield United | 1-1 | Rotherham United |
| 1st Round 1st Leg | Shrewsbury Town | 3-0 | Notts. County |
| 1st Round 1st Leg | 0-1 |
| 1st Round 1st Leg | Walsall | 1-2 | Port Vale |
| 1st Round 1st Leg | Wolverhampton Wanderers | 1-0 | Lincoln City |
| 1st Round 1st Leg | Wrexham | 0-0 | Wigan Athletic |
21st August 1989
| 1st Round 1st Leg | 1-0 |