9th April 1989
| Final | Nottingham Forest | 3-1 | Luton Town |
1st March 1989
| Semi Final 2nd Leg | Luton Town | 2-0 | West Ham United |
26th February 1989
| Semi Final 2nd Leg | Bristol City | 0-1 | Nottingham Forest |
15th February 1989
| Semi Final 1st Leg | Nottingham Forest | 1-1 | Bristol City |
12th February 1989
| Semi Final 1st Leg | West Ham United | 0-3 | Luton Town |
25th January 1989
| Quarter Final Replay | Southampton | 1-2 | Luton Town |
18th January 1989
| Quarter Final | Bradford City | 0-1 | Bristol City |
| Quarter Final | Luton Town | 1-1 | Southampton |
| Quarter Final | Nottingham Forest | 5-2 | Queens Park Rangers |
| Quarter Final | West Ham United | 2-1 | Aston Villa |
14th December 1988
| 4th Round | Bradford City | 3-1 | Everton |
| 4th Round Replay | Nottingham Forest | 2-1 | Leicester City |
| 4th Round Replay | 0-1 | Queens Park Rangers |
30th November 1988
| 4th Round | Aston Villa | 6-2 | Ipswich Town |
| 4th Round | Leicester City | 0-0 | Nottingham Forest |
| 4th Round | Queens Park Rangers | 0-0 |
| 4th Round | West Ham United | 4-1 | Liverpool |
29th November 1988
| 4th Round | Bristol City | 1-0 |
| 4th Round | Luton Town | 3-1 | Manchester City |
| 3rd Round Replay | Oldham Athletic | 0-2 | Everton |
| 4th Round | Southampton | 2-1 | Tottenham Hotspur |
23rd November 1988
| 3rd Round 2nd Replay | Liverpool | 2-1 | Arsenal |
22nd November 1988
| 3rd Round Replay | Scunthorpe United | 0-1 | Bradford City |
| 3rd Round Replay | Southampton | 1-0 |
9th November 1988
| 3rd Round Replay | Arsenal | 0-0 | Liverpool |
| 3rd Round Replay | Blackburn Rovers | 1-2 | Tottenham Hotspur |
8th November 1988
| 3rd Round | Everton | 1-1 | Oldham Athletic |
2nd November 1988
| 3rd Round | Aston Villa | 3-1 | Millwall |
| 3rd Round | Bradford City | 1-1 | Scunthorpe United |
| 3rd Round | Leeds United | 0-2 | Luton Town |
| 3rd Round | Leicester City | 2-0 | Norwich City |
| 3rd Round | Liverpool | 1-1 | Arsenal |
| 3rd Round | Manchester City | 4-2 | Sheffield United |
| 3rd Round | Nottingham Forest | 3-2 | Coventry City |
| 3rd Round | Queens Park Rangers | 2-1 | Charlton Athletic |
| 3rd Round | 2-2 | Southampton |
| 3rd Round | 2-1 | Manchester United |
1st November 1988
| 3rd Round | Bristol City | 4-1 | Crystal Palace |
| 3rd Round | Ipswich Town | 2-0 | Leyton Orient |
| 3rd Round | Tottenham Hotspur | 0-0 | Blackburn Rovers |
| 3rd Round | 1-0 | Blackpool |
| 3rd Round | West Ham United | 5-0 | Derby County |
12th October 1988
| 2nd Round 2nd Leg | Arsenal | 3-0 | Hull City |
| 2nd Round 2nd Leg | Aston Villa | 5-0 | Birmingham City |
| 2nd Round 2nd Leg | Bradford City | 2-1 | Reading |
| 2nd Round 2nd Leg | Brentford | 4-3 | Blackburn Rovers |
| 2nd Round 2nd Leg | Chelsea | 2-2 | Scunthorpe United |
| 2nd Round 2nd Leg | 0-4 | Nottingham Forest |
| 2nd Round 2nd Leg | Crystal Palace | 2-0 | Swindon Town |
| 2nd Round 2nd Leg | Leeds United | 3-1 | Peterborough United |
| 2nd Round 2nd Leg | Manchester United | 5-0 | Rotherham United |
| 2nd Round 2nd Leg | Newcastle United | 2-0 | Sheffield United |
| 2nd Round 2nd Leg | Plymouth Argyle | 3-6 | Manchester City |
| 2nd Round 2nd Leg | 3-1 | Portsmouth |
| 2nd Round 2nd Leg | Sheffield Wednesday | 3-1 | Blackpool |
| 2nd Round 2nd Leg | Walsall | 1-3 | Liverpool |
| 2nd Round 2nd Leg | West Ham United | 2-1 | Sunderland |
| 2nd Round 2nd Leg | 0-1 | Barnsley |
11th October 1988
| 2nd Round 2nd Leg | Bristol City | 2-0 | Oxford United |
| 2nd Round 2nd Leg | Burnley | 0-1 | Luton Town |
| 2nd Round 2nd Leg | 2-2 | Everton |
| 2nd Round 2nd Leg | Cardiff City | 1-4 | Queens Park Rangers |
| 2nd Round 2nd Leg | Charlton Athletic | 2-1 | Northampton Town |
| 2nd Round 2nd Leg | Coventry City | 3-1 | AFC Bournemouth |
| 2nd Round 2nd Leg | 1-3 | Millwall |
| 2nd Round 2nd Leg | Ipswich Town | 3-0 | Port Vale |
| 2nd Round 2nd Leg | Oldham Athletic | 4-0 |
| 2nd Round 2nd Leg | Preston North End | 0-3 | Norwich City |
| 2nd Round 2nd Leg | Southampton | 3-1 | Lincoln City |
| 2nd Round 2nd Leg | 1-2 | Derby County |
| 2nd Round 2nd Leg | Stoke City | 1-2 | Leyton Orient |
| 2nd Round 2nd Leg | Tottenham Hotspur | 2-1 | Notts. County |
| 2nd Round 2nd Leg | 1-0 | Middlesbrough |
| 2nd Round 2nd Leg | Watford | 2-2 | Leicester City |
28th September 1988
| 2nd Round 1st Leg | Derby County | 1-0 |
| 2nd Round 1st Leg | Hull City | 1-2 | Arsenal |
| 2nd Round 1st Leg | Leicester City | 4-1 | Watford |
| 2nd Round 1st Leg | Lincoln City | 1-1 | Southampton |
| 2nd Round 1st Leg | Liverpool | 1-0 | Walsall |
| 2nd Round 1st Leg | Manchester City | 1-0 | Plymouth Argyle |
| 2nd Round 1st Leg | Middlesbrough | 0-0 |
| 2nd Round 1st Leg | Norwich City | 2-0 | Preston North End |
| 2nd Round 1st Leg | Nottingham Forest | 6-0 |
| 2nd Round 1st Leg | Oxford United | 2-4 | Bristol City |
| 2nd Round 1st Leg | Queens Park Rangers | 3-0 | Cardiff City |
| 2nd Round 1st Leg | Reading | 1-1 | Bradford City |
| 2nd Round 1st Leg | Rotherham United | 0-1 | Manchester United |
27th September 1988
| 2nd Round 1st Leg | Barnsley | 0-2 |
| 2nd Round 1st Leg | Birmingham City | 0-2 | Aston Villa |
| 2nd Round 1st Leg | Blackburn Rovers | 3-1 | Brentford |
| 2nd Round 1st Leg | Blackpool | 2-0 | Sheffield Wednesday |
| 2nd Round 1st Leg | AFC Bournemouth | 0-4 | Coventry City |
| 2nd Round 1st Leg | 2-0 | Oldham Athletic |
| 2nd Round 1st Leg | Everton | 3-0 |
| 2nd Round 1st Leg | Leyton Orient | 1-2 | Stoke City |
| 2nd Round 1st Leg | Luton Town | 1-1 | Burnley |
| 2nd Round 1st Leg | Millwall | 3-0 |
| 2nd Round 1st Leg | Northampton Town | 1-1 | Charlton Athletic |
| 2nd Round 1st Leg | Notts. County | 1-1 | Tottenham Hotspur |
| 2nd Round 1st Leg | Peterborough United | 1-2 | Leeds United |
| 2nd Round 1st Leg | Portsmouth | 2-2 |
| 2nd Round 1st Leg | Scunthorpe United | 4-1 | Chelsea |
| 2nd Round 1st Leg | Sheffield United | 3-0 | Newcastle United |
| 2nd Round 1st Leg | Sunderland | 0-3 | West Ham United |
| 2nd Round 1st Leg | Swindon Town | 1-2 | Crystal Palace |
26th September 1988
| 2nd Round 1st Leg | Port Vale | 1-0 | Ipswich Town |
20th September 1988
| 1st Round 2nd Leg | Swansea City | 0-2 | Cardiff City |
7th September 1988
| 1st Round 2nd Leg | Brighton & Hove Albion | 0-1 |
| 1st Round 2nd Leg | Bristol Rovers | 0-0 | AFC Bournemouth |
| 1st Round 2nd Leg | 3-1 | Bolton Wanderers |
| 1st Round 2nd Leg | Exeter City | 0-1 | Bristol City |
| 1st Round 2nd Leg | Lincoln City | 2-1 | Crewe Alexandra |
| 1st Round 2nd Leg | Peterborough United | 0-2 | West Bromwich Albion |
| 1st Round 2nd Leg | Reading | 3-1 |
6th September 1988
| 1st Round 2nd Leg | Aldershot Town | 0-0 | Leyton Orient |
| 1st Round 2nd Leg | Birmingham City | 1-0 | Wolverhampton Wanderers |
| 1st Round 2nd Leg | Blackpool | 3-0 | Carlisle United |
| 1st Round 2nd Leg | Brentford | 1-0 | Fulham |
| 1st Round 2nd Leg | Burnley | 2-1 |
| 1st Round 2nd Leg | Chesterfield | 1-1 | Port Vale |
| 1st Round 2nd Leg | 2-0 |
| 1st Round 2nd Leg | 3-1 | Cambridge United |
| 1st Round 2nd Leg | FC Halifax Town | 2-2 |
| 1st Round 2nd Leg | Huddersfield Town | 2-2 | Scunthorpe United |
| 1st Round 2nd Leg | Mansfield Town | 1-0 | Notts. County |
| 1st Round 2nd Leg | Northampton Town | 5-0 | Colchester United |
| 1st Round 2nd Leg | Plymouth Argyle | 3-2 |
| 1st Round 2nd Leg | Preston North End | 1-0 | Wigan Athletic |
| 1st Round 2nd Leg | Rotherham United | 1-0 | Grimsby Town |
| 1st Round 2nd Leg | Sheffield United | 2-0 | Hartlepool United |
| 1st Round 2nd Leg | Sunderland | 4-0 |
| 1st Round 2nd Leg | Walsall | 3-0 | Shrewsbury Town |
| 1st Round 2nd Leg | Wrexham | 2-2 |
5th September 1988
| 1st Round 2nd Leg | 1-1 |
31st August 1988
| 1st Round 1st Leg | 1-1 | FC Halifax Town |
| 1st Round 1st Leg | West Bromwich Albion | 0-3 | Peterborough United |
30th August 1988
| 1st Round 1st Leg | Bolton Wanderers | 1-0 |
| 1st Round 1st Leg | AFC Bournemouth | 1-0 | Bristol Rovers |
| 1st Round 1st Leg | Bristol City | 1-0 | Exeter City |
| 1st Round 1st Leg | 2-1 | Wrexham |
| 1st Round 1st Leg | Cambridge United | 1-2 |
| 1st Round 1st Leg | Cardiff City | 0-1 | Swansea City |
| 1st Round 1st Leg | Carlisle United | 1-1 | Blackpool |
| 1st Round 1st Leg | Colchester United | 0-0 | Northampton Town |
| 1st Round 1st Leg | Crewe Alexandra | 1-1 | Lincoln City |
| 1st Round 1st Leg | 1-1 |
| 1st Round 1st Leg | Fulham | 2-2 | Brentford |
| 1st Round 1st Leg | Grimsby Town | 0-1 | Rotherham United |
| 1st Round 1st Leg | Hartlepool United | 2-2 | Sheffield United |
| 1st Round 1st Leg | Leyton Orient | 2-0 | Aldershot Town |
| 1st Round 1st Leg | Notts. County | 5-0 | Mansfield Town |
| 1st Round 1st Leg | Port Vale | 3-2 | Chesterfield |
| 1st Round 1st Leg | 3-3 | Burnley |
| 1st Round 1st Leg | Scunthorpe United | 3-2 | Huddersfield Town |
| 1st Round 1st Leg | Shrewsbury Town | 2-2 | Walsall |
| 1st Round 1st Leg | 2-0 | Brighton & Hove Albion |
| 1st Round 1st Leg | 0-1 | Reading |
| 1st Round 1st Leg | Wolverhampton Wanderers | 3-2 | Birmingham City |
| 1st Round 1st Leg | 0-0 | Sunderland |
29th August 1988
| 1st Round 1st Leg | 0-3 | Plymouth Argyle |
| 1st Round 1st Leg | 0-1 |
| 1st Round 1st Leg | Wigan Athletic | 0-0 | Preston North End |