20th May 1989
| Final | Liverpool | 3-2 | Everton |
7th May 1989
| Semi Final | Liverpool | 3-1 | Nottingham Forest |
15th April 1989
| Semi Final | Everton | 1-0 | Norwich City |
22nd March 1989
| 6th Round Replay | Norwich City | 3-1 | West Ham United |
19th March 1989
| 6th Round | Everton | 1-0 |
18th March 1989
| 6th Round | Liverpool | 4-0 | Brentford |
| 6th Round | Manchester United | 0-1 | Nottingham Forest |
| 6th Round | West Ham United | 0-0 | Norwich City |
22nd February 1989
| 5th Round Replay | Manchester United | 1-0 | AFC Bournemouth |
19th February 1989
| 5th Round | Watford | 0-3 | Nottingham Forest |
18th February 1989
| 5th Round | Barnsley | 0-1 | Everton |
| 5th Round | Blackburn Rovers | 0-2 | Brentford |
| 5th Round | AFC Bournemouth | 1-1 | Manchester United |
| 5th Round | Charlton Athletic | 0-1 | West Ham United |
| 5th Round | Hull City | 2-3 | Liverpool |
| 5th Round | Norwich City | 3-2 | Sheffield United |
| 5th Round | 3-1 | Grimsby Town |
1st February 1989
| 4th Round Replay | Reading | 1-2 | Grimsby Town |
| 4th Round Replay | West Ham United | 1-0 | Swindon Town |
31st January 1989
| 4th Round Replay | Barnsley | 2-1 | Stoke City |
| 4th Round Replay | AFC Bournemouth | 5-2 | Hartlepool United |
| 4th Round Replay | Colchester United | 0-2 | Sheffield United |
| 4th Round Replay | Everton | 4-0 | Plymouth Argyle |
29th January 1989
| 4th Round | Millwall | 0-2 | Liverpool |
28th January 1989
| 4th Round | Aston Villa | 0-1 |
| 4th Round | Blackburn Rovers | 2-1 | Sheffield Wednesday |
| 4th Round | Bradford City | 1-2 | Hull City |
| 4th Round | Brentford | 3-1 | Manchester City |
| 4th Round | Charlton Athletic | 2-1 |
| 4th Round | Grimsby Town | 1-1 | Reading |
| 4th Round | Hartlepool United | 1-1 | AFC Bournemouth |
| 4th Round | Manchester United | 4-0 | Oxford United |
| 4th Round | Norwich City | 8-0 | Sutton United |
| 4th Round | Nottingham Forest | 2-0 | Leeds United |
| 4th Round | Plymouth Argyle | 1-1 | Everton |
| 4th Round | Sheffield United | 3-3 | Colchester United |
| 4th Round | Stoke City | 3-3 | Barnsley |
| 4th Round | Swindon Town | 0-0 | West Ham United |
| 4th Round | Watford | 2-1 | Derby County |
23rd January 1989
| 3rd Round 2nd Replay | Manchester United | 3-0 | Queens Park Rangers |
18th January 1989
| 3rd Round 3rd Replay | Watford | 1-0 | Newcastle United |
16th January 1989
| 3rd Round 2nd Replay | Newcastle United | 0-0 | Watford |
11th January 1989
| 3rd Round Replay | Arsenal | 0-1 | West Ham United |
| 3rd Round Replay | Everton | 1-0 | West Bromwich Albion |
| 3rd Round Replay | Oxford United | 2-0 | Sunderland |
| 3rd Round Replay | Queens Park Rangers | 2-2 | Manchester United |
| 3rd Round Replay | Reading | 2-1 |
10th January 1989
| 3rd Round Replay | Brentford | 1-0 | Walsall |
| 3rd Round Replay | FC Halifax Town | 2-3 |
| 3rd Round Replay | Southampton | 1-2 | Derby County |
| 3rd Round Replay | Swindon Town | 2-0 | Portsmouth |
| 3rd Round Replay | Watford | 2-2 | Newcastle United |
8th January 1989
| 3rd Round | Port Vale | 1-3 | Norwich City |
| 3rd Round | West Ham United | 2-2 | Arsenal |
7th January 1989
| 3rd Round | Barnsley | 4-0 | Chelsea |
| 3rd Round | Birmingham City | 0-1 |
| 3rd Round | Blackpool | 0-1 | AFC Bournemouth |
| 3rd Round | Bradford City | 1-0 | Tottenham Hotspur |
| 3rd Round | Brighton & Hove Albion | 1-2 | Leeds United |
| 3rd Round | Cardiff City | 1-2 | Hull City |
| 3rd Round | Carlisle United | 0-3 | Liverpool |
| 3rd Round | Charlton Athletic | 2-1 | Oldham Athletic |
| 3rd Round | Crewe Alexandra | 2-3 | Aston Villa |
| 3rd Round | Derby County | 1-1 | Southampton |
| 3rd Round | Hartlepool United | 1-0 | Bristol City |
| 3rd Round | Huddersfield Town | 0-1 | Sheffield United |
| 3rd Round | 1-1 | FC Halifax Town |
| 3rd Round | Manchester City | 1-0 | Leicester City |
| 3rd Round | Manchester United | 0-0 | Queens Park Rangers |
| 3rd Round | Middlesbrough | 1-2 | Grimsby Town |
| 3rd Round | Millwall | 3-2 | Luton Town |
| 3rd Round | Newcastle United | 0-0 | Watford |
| 3rd Round | Nottingham Forest | 3-0 | Ipswich Town |
| 3rd Round | Plymouth Argyle | 2-0 | Cambridge United |
| 3rd Round | Portsmouth | 1-1 | Swindon Town |
| 3rd Round | Sheffield Wednesday | 5-1 |
| 3rd Round | Shrewsbury Town | 0-3 | Colchester United |
| 3rd Round | Stoke City | 1-0 | Crystal Palace |
| 3rd Round | Sunderland | 1-1 | Oxford United |
| 3rd Round | Sutton United | 2-1 | Coventry City |
| 3rd Round | 1-1 | Reading |
| 3rd Round | Walsall | 1-1 | Brentford |
| 3rd Round | 0-1 | Blackburn Rovers |
| 3rd Round | West Bromwich Albion | 1-1 | Everton |
22nd December 1988
| 2nd Round 3rd Replay | Bristol City | 1-0 | Aldershot Town |
20th December 1988
| 2nd Round 2nd Replay | Aldershot Town | 2-2 | Bristol City |
14th December 1988
| 2nd Round Replay | Brentford | 3-2 | Peterborough United |
| 2nd Round Replay | Maidstone United | 1-2 | Reading |
| 2nd Round Replay | 1-0 |
| 2nd Round Replay | 3-2 |
13th December 1988
| 2nd Round Replay | Bristol City | 0-0 | Aldershot Town |
| 2nd Round Replay | Swansea City | 1-3 | Colchester United |
11th December 1988
| 2nd Round | 1-3 | Sheffield United |
| 2nd Round | 1-4 | Cardiff City |
10th December 1988
| 2nd Round | Aldershot Town | 1-1 | Bristol City |
| 2nd Round | 0-3 | FC Halifax Town |
| 2nd Round | 0-1 | Sutton United |
| 2nd Round | 0-0 |
| 2nd Round | Blackpool | 3-0 |
| 2nd Round | 1-0 | Cambridge United |
| 2nd Round | Bolton Wanderers | 1-2 | Port Vale |
| 2nd Round | Colchester United | 2-2 | Swansea City |
| 2nd Round | Grimsby Town | 3-2 | Rotherham United |
| 2nd Round | Hartlepool United | 1-0 | Notts. County |
| 2nd Round | Huddersfield Town | 1-0 |
| 2nd Round | 2-1 | Bristol Rovers |
| 2nd Round | 1-2 |
| 2nd Round | Peterborough United | 0-0 | Brentford |
| 2nd Round | Reading | 1-1 | Maidstone United |
| 2nd Round | 0-3 | Crewe Alexandra |
| 2nd Round | 0-1 | Carlisle United |
| 2nd Round | 1-1 |
28th November 1988
| 1st Round Replay | Chesterfield | 2-3 | Bolton Wanderers |
| 1st Round Replay | 3-4 | Huddersfield Town |
| 1st Round 2nd Replay | Leyton Orient | 0-1 |
23rd November 1988
| 1st Round Replay | 2-3 |
| 1st Round Replay | Leyton Orient | 2-2 |
| 1st Round Replay | Peterborough United | 1-0 |
22nd November 1988
| 1st Round Replay | 1-2 |
| 1st Round Replay | Carlisle United | 4-1 |
| 1st Round Replay | Crewe Alexandra | 3-2 |
| 1st Round Replay | Sheffield United | 2-1 | Mansfield Town |
| 1st Round Replay | 3-0 | Preston North End |
| 1st Round Replay | Wrexham | 2-3 |
20th November 1988
| 1st Round | Bristol Rovers | 3-0 |
19th November 1988
| 1st Round | Aldershot Town | 1-0 |
| 1st Round | 3-2 | Lincoln City |
| 1st Round | 2-0 |
| 1st Round | Blackpool | 2-1 | Scunthorpe United |
| 1st Round | 2-1 | Exeter City |
| 1st Round | Bolton Wanderers | 0-0 | Chesterfield |
| 1st Round | Brentford | 2-0 |
| 1st Round | Bristol City | 3-1 |
| 1st Round | Burnley | 0-2 |
| 1st Round | Cardiff City | 3-0 |
| 1st Round | 0-4 | Sutton United |
| 1st Round | 1-2 | Notts. County |
| 1st Round | 0-0 |
| 1st Round | 1-1 | Leyton Orient |
| 1st Round | 0-2 |
| 1st Round | Fulham | 0-1 | Colchester United |
| 1st Round | 3-3 | Peterborough United |
| 1st Round | Grimsby Town | 1-0 | Wolverhampton Wanderers |
| 1st Round | 0-1 |
| 1st Round | FC Halifax Town | 1-0 |
| 1st Round | Hartlepool United | 2-0 | Wigan Athletic |
| 1st Round | Huddersfield Town | 1-1 |
| 1st Round | 2-1 |
| 1st Round | Mansfield Town | 1-1 | Sheffield United |
| 1st Round | Newport County | 1-2 | Maidstone United |
| 1st Round | Preston North End | 1-1 |
| 1st Round | Reading | 4-2 |
| 1st Round | Rotherham United | 3-1 | Barrow |
| 1st Round | 2-2 | Wrexham |
| 1st Round | 2-1 |
| 1st Round | 0-2 | Port Vale |
| 1st Round | 2-2 | Crewe Alexandra |
| 1st Round | Swansea City | 3-1 | Northampton Town |
| 1st Round | 1-1 | Carlisle United |
| 1st Round | 2-2 |
| 1st Round | 1-4 |
| 1st Round | 3-0 |
| 1st Round | 1-4 | Cambridge United |
| 1st Round | 3-2 |