17th May 1990
| Final Replay | Manchester United | 1-0 | Crystal Palace |
12th May 1990
| Final | Manchester United | 3-3 | Crystal Palace |
11th April 1990
| Semi Final Replay | Manchester United | 2-1 | Oldham Athletic |
8th April 1990
| Semi Final | Oldham Athletic | 3-3 | Manchester United |
| Semi Final | Crystal Palace | 4-3 | Liverpool |
14th March 1990
| 6th Round | Oldham Athletic | 3-0 | Aston Villa |
| 6th Round Replay | Liverpool | 1-0 | Queens Park Rangers |
11th March 1990
| 6th Round | Sheffield United | 0-1 | Manchester United |
| 6th Round | Queens Park Rangers | 2-2 | Liverpool |
10th March 1990
| 5th Round 2nd Replay | Oldham Athletic | 2-1 | Everton |
| 6th Round | Cambridge United | 0-1 | Crystal Palace |
5th March 1990
| 5th Round 2nd Replay | Barnsley | 0-1 | Sheffield United |
27th February 1990
| 5th Round 2nd Replay | Cambridge United | 5-1 | Bristol City |
26th February 1990
| 5th Round 2nd Replay | Queens Park Rangers | 3-0 | Blackpool |
21st February 1990
| 5th Round Replay | Barnsley | 0-0 | Sheffield United |
| 5th Round Replay | Cambridge United | 1-1 | Bristol City |
| 5th Round Replay | Queens Park Rangers | 0-0 | Blackpool |
| 5th Round Replay | Everton | 1-1 | Oldham Athletic |
18th February 1990
| 5th Round | Blackpool | 2-2 | Queens Park Rangers |
| 5th Round | Newcastle United | 2-3 | Manchester United |
| 5th Round | Sheffield United | 2-2 | Barnsley |
17th February 1990
| 5th Round | Bristol City | 0-0 | Cambridge United |
| 5th Round | Crystal Palace | 1-0 |
| 5th Round | Liverpool | 3-0 | Southampton |
| 5th Round | Oldham Athletic | 2-2 | Everton |
| 5th Round | West Bromwich Albion | 0-2 | Aston Villa |
31st January 1990
| 4th Round Replay | Liverpool | 3-1 | Norwich City |
| 4th Round Replay | Newcastle United | 4-1 | Reading |
| 4th Round Replay | Queens Park Rangers | 2-0 | Arsenal |
30th January 1990
| 4th Round Replay | Watford | 1-2 | Sheffield United |
| 4th Round Replay | Cambridge United | 1-0 | Millwall |
28th January 1990
| 4th Round | 0-1 | Manchester United |
| 4th Round | Norwich City | 0-0 | Liverpool |
| 4th Round | Sheffield Wednesday | 1-2 | Everton |
27th January 1990
| 4th Round | Arsenal | 0-0 | Queens Park Rangers |
| 4th Round | Aston Villa | 6-0 | Port Vale |
| 4th Round | Barnsley | 2-0 | Ipswich Town |
| 4th Round | Blackpool | 1-0 |
| 4th Round | Bristol City | 3-1 | Chelsea |
| 4th Round | Crystal Palace | 4-0 | Huddersfield Town |
| 4th Round | Millwall | 1-1 | Cambridge United |
| 4th Round | Oldham Athletic | 2-1 | Brighton & Hove Albion |
| 4th Round | Reading | 3-3 | Newcastle United |
| 4th Round | 3-0 | Northampton Town |
| 4th Round | Sheffield United | 1-1 | Watford |
| 4th Round | Southampton | 1-0 | Oxford United |
| 4th Round | West Bromwich Albion | 1-0 | Charlton Athletic |
17th January 1990
| 3rd Round 2nd Replay | Everton | 1-0 | Middlesbrough |
15th January 1990
| 3rd Round 2nd Replay | Millwall | 3-1 | Manchester City |
10th January 1990
| 3rd Round Replay | Queens Park Rangers | 2-0 | Cardiff City |
| 3rd Round Replay | Oldham Athletic | 1-0 | Birmingham City |
| 3rd Round Replay | Norwich City | 2-0 | Exeter City |
| 3rd Round Replay | Everton | 1-1 | Middlesbrough |
| 3rd Round Replay | Derby County | 2-3 | Port Vale |
| 3rd Round Replay | Crewe Alexandra | 0-2 | Chelsea |
| 3rd Round Replay | Bradford City | 0-3 | Charlton Athletic |
| 3rd Round Replay | Aston Villa | 3-1 | Blackburn Rovers |
9th January 1990
| 3rd Round Replay | Millwall | 1-1 | Manchester City |
| 3rd Round Replay | Liverpool | 8-0 | Swansea City |
| 3rd Round Replay | 1-3 | Cambridge United |
7th January 1990
| 3rd Round | Charlton Athletic | 1-1 | Bradford City |
| 3rd Round | Nottingham Forest | 0-1 | Manchester United |
| 3rd Round | Port Vale | 1-1 | Derby County |
6th January 1990
| 3rd Round | Birmingham City | 1-1 | Oldham Athletic |
| 3rd Round | Blackburn Rovers | 2-2 | Aston Villa |
| 3rd Round | Blackpool | 1-0 | Burnley |
| 3rd Round | Brighton & Hove Albion | 4-1 | Luton Town |
| 3rd Round | Bristol City | 2-1 | Swindon Town |
| 3rd Round | Cambridge United | 0-0 |
| 3rd Round | Cardiff City | 0-0 | Queens Park Rangers |
| 3rd Round | Chelsea | 1-1 | Crewe Alexandra |
| 3rd Round | Crystal Palace | 2-1 | Portsmouth |
| 3rd Round | Exeter City | 1-1 | Norwich City |
| 3rd Round | 2-1 | Walsall |
| 3rd Round | Huddersfield Town | 3-1 | Grimsby Town |
| 3rd Round | Hull City | 0-1 | Newcastle United |
| 3rd Round | Leeds United | 0-1 | Ipswich Town |
| 3rd Round | Leicester City | 1-2 | Barnsley |
| 3rd Round | Manchester City | 0-0 | Millwall |
| 3rd Round | Middlesbrough | 0-0 | Everton |
| 3rd Round | Northampton Town | 1-0 | Coventry City |
| 3rd Round | Plymouth Argyle | 0-1 | Oxford United |
| 3rd Round | Reading | 2-1 | Sunderland |
| 3rd Round | 1-0 |
| 3rd Round | Sheffield United | 2-0 | AFC Bournemouth |
| 3rd Round | Stoke City | 0-1 | Arsenal |
| 3rd Round | Swansea City | 0-0 | Liverpool |
| 3rd Round | 1-0 | West Ham United |
| 3rd Round | Tottenham Hotspur | 1-3 | Southampton |
| 3rd Round | Watford | 2-0 | Wigan Athletic |
| 3rd Round | West Bromwich Albion | 2-0 |
| 3rd Round | Wolverhampton Wanderers | 1-2 | Sheffield Wednesday |
22nd December 1989
| 2nd Round 3rd Replay | 1-2 | Reading |
19th December 1989
| 2nd Round 2nd Replay | Reading | 0-0 |
18th December 1989
| 2nd Round 2nd Replay | Burnley | 5-0 | Scunthorpe United |
13th December 1989
| 2nd Round Replay | 1-1 | Reading |
| 2nd Round Replay | Exeter City | 3-2 | Maidstone United |
| 2nd Round Replay | 0-2 | Crewe Alexandra |
| 2nd Round Replay | 0-1 | Northampton Town |
12th December 1989
| 2nd Round Replay | 0-1 | Cardiff City |
| 2nd Round Replay | Burnley | 1-1 | Scunthorpe United |
9th December 1989
| 2nd Round | 2-3 |
| 2nd Round | Blackpool | 3-0 |
| 2nd Round | Bristol City | 2-1 | Fulham |
| 2nd Round | Cambridge United | 3-1 |
| 2nd Round | Cardiff City | 2-2 |
| 2nd Round | Chesterfield | 0-2 | Huddersfield Town |
| 2nd Round | Colchester United | 0-2 | Birmingham City |
| 2nd Round | Crewe Alexandra | 1-1 |
| 2nd Round | 3-0 | FC Halifax Town |
| 2nd Round | Grimsby Town | 1-0 |
| 2nd Round | 3-2 |
| 2nd Round | Northampton Town | 0-0 |
| 2nd Round | Reading | 0-0 |
| 2nd Round | 3-0 | Lincoln City |
| 2nd Round | Scunthorpe United | 2-2 | Burnley |
| 2nd Round | Swansea City | 3-1 | Peterborough United |
| 2nd Round | Walsall | 1-0 | Rotherham United |
| 2nd Round | 2-0 | Preston North End |
| 2nd Round | Wigan Athletic | 2-0 | Carlisle United |
| 2nd Round | Maidstone United | 1-1 | Exeter City |
27th November 1989
| 1st Round 2nd Replay | Bristol Rovers | 0-1 | Reading |
22nd November 1989
| 1st Round Replay | 1-0 |
| 1st Round Replay | 4-0 | Sutton United |
| 1st Round Replay | 1-2 | Burnley |
| 1st Round Replay | Fulham | 2-1 |
| 1st Round Replay | Exeter City | 4-1 |
21st November 1989
| 1st Round Replay | Reading | 1-1 | Bristol Rovers |
| 1st Round Replay | 0-1 | Peterborough United |
| 1st Round Replay | 3-2 | Macclesfield Town |
| 1st Round Replay | 1-2 | Rotherham United |
19th November 1989
| 1st Round | 2-2 | Fulham |
| 1st Round | Maidstone United | 2-1 |
| 1st Round | Wigan Athletic | 2-0 | Mansfield Town |
18th November 1989
| 1st Round | Aldershot Town | 0-1 | Cambridge United |
| 1st Round | 1-0 |
| 1st Round | 3-0 |
| 1st Round | 2-0 |
| 1st Round | Blackpool | 2-1 | Bolton Wanderers |
| 1st Round | Brentford | 0-1 | Colchester United |
| 1st Round | Bristol City | 2-0 | Barnet |
| 1st Round | Bristol Rovers | 1-1 | Reading |
| 1st Round | Burnley | 1-1 |
| 1st Round | Cardiff City | 1-0 |
| 1st Round | Carlisle United | 3-0 | Wrexham |
| 1st Round | Crewe Alexandra | 2-0 |
| 1st Round | 6-2 |
| 1st Round | 1-1 | Exeter City |
| 1st Round | 1-0 | Notts. County |
| 1st Round | 0-1 |
| 1st Round | 0-0 |
| 1st Round | 1-0 |
| 1st Round | Hartlepool United | 0-2 | Huddersfield Town |
| 1st Round | 0-1 | Northampton Town |
| 1st Round | 2-3 | Swansea City |
| 1st Round | Leyton Orient | 0-1 | Birmingham City |
| 1st Round | Lincoln City | 1-0 |
| 1st Round | Macclesfield Town | 1-1 |
| 1st Round | 0-1 |
| 1st Round | Peterborough United | 1-1 |
| 1st Round | Preston North End | 1-0 |
| 1st Round | 1-3 |
| 1st Round | Rotherham United | 0-0 |
| 1st Round | 0-1 |
| 1st Round | Scunthorpe United | 4-1 |
| 1st Round | Shrewsbury Town | 2-3 | Chesterfield |
| 1st Round | 1-2 |
| 1st Round | 2-3 | FC Halifax Town |
| 1st Round | Sutton United | 1-1 |
| 1st Round | 0-3 | Walsall |
| 1st Round | 1-2 | Grimsby Town |