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| 1st(1st leg) | Port Vale FC | - | Wimbledon FC | 1:2 | ||
| 2nd (2nd leg) | Wimbledon FC | - | Port Vale FC | 3:0 | ||
| 1st(1st leg): 18/09/1989 | 2nd (2nd leg): 04/10/1989 | Winner: Wimbledon FC | ||||
| 1st(1st leg) | Arsenal FC | - | Plymouth Argyle | 2:0 | ||
| 2nd (2nd leg) | Plymouth Argyle | - | Arsenal FC | 1:6 | ||
| 1st(1st leg): 19/09/1989 | 2nd (2nd leg): 03/10/1989 | Winner: Arsenal FC | ||||
| 1st(1st leg) | Barnsley FC | - | Blackpool FC | 1:1 | ||
| 2nd (2nd leg) | Blackpool FC | - | Barnsley FC | 5:4 pso | ||
| 1st(1st leg): 19/09/1989 | 2nd (2nd leg): 03/10/1989 | Winner: Blackpool FC | ||||
| 1st(1st leg) | Birmingham City | - | West Ham United | 1:2 | ||
| 2nd (2nd leg) | West Ham United | - | Birmingham City | 1:1 | ||
| 1st(1st leg): 19/09/1989 | 2nd (2nd leg): 04/10/1989 | Winner: West Ham United | ||||
| 1st(1st leg) | Bolton Wanderers | - | Watford FC | 2:1 | ||
| 2nd (2nd leg) | Watford FC | - | Bolton Wanderers | 1:1 | ||
| 1st(1st leg): 19/09/1989 | 2nd (2nd leg): 03/10/1989 | Winner: Bolton Wanderers | ||||
| 1st(1st leg) | Brentford FC | - | Manchester City | 2:1 | ||
| 2nd (2nd leg) | Manchester City | - | Brentford FC | 4:1 | ||
| 1st(1st leg): 19/09/1989 | 2nd (2nd leg): 04/10/1989 | Winner: Manchester City | ||||
| 1st(1st leg) | Cambridge United | - | Derby County | 2:1 | ||
| 2nd (2nd leg) | Derby County | - | Cambridge United | 5:0 | ||
| 1st(1st leg): 19/09/1989 | 2nd (2nd leg): 04/10/1989 | Winner: Derby County | ||||
| 1st(1st leg) | Chelsea FC | - | Scarborough FC | 1:1 | ||
| 2nd (2nd leg) | Scarborough FC | - | Chelsea FC | 3:2 aet | ||
| 1st(1st leg): 19/09/1989 | 2nd (2nd leg): 04/10/1989 | Winner: Scarborough FC | ||||
| 1st(1st leg) | Crewe Alexandra | - | AFC Bournemouth | 0:1 | ||
| 2nd (2nd leg) | AFC Bournemouth | - | Crewe Alexandra | 0:0 | ||
| 1st(1st leg): 19/09/1989 | 2nd (2nd leg): 03/10/1989 | Winner: AFC Bournemouth | ||||
| 1st(1st leg) | Crystal Palace | - | Leicester City | 1:2 | ||
| 2nd (2nd leg) | Leicester City | - | Crystal Palace | 2:3 aet | ||
| 1st(1st leg): 19/09/1989 | 2nd (2nd leg): 04/10/1989 | Winner: Crystal Palace | ||||
| 1st(1st leg) | Grimsby Town | - | Coventry City | 3:1 | ||
| 2nd (2nd leg) | Coventry City | - | Grimsby Town | 3:0 | ||
| 1st(1st leg): 19/09/1989 | 2nd (2nd leg): 04/10/1989 | Winner: Coventry City | ||||
| 1st(1st leg) | Ipswich Town | - | Tranmere Rovers | 0:1 | ||
| 2nd (2nd leg) | Tranmere Rovers | - | Ipswich Town | 1:0 | ||
| 1st(1st leg): 19/09/1989 | 2nd (2nd leg): 03/10/1989 | Winner: Tranmere Rovers | ||||
| 1st(1st leg) | Leyton Orient | - | Everton FC | 0:2 | ||
| 2nd (2nd leg) | Everton FC | - | Leyton Orient | 2:2 | ||
| 1st(1st leg): 19/09/1989 | 2nd (2nd leg): 03/10/1989 | Winner: Everton FC | ||||
| 1st(1st leg) | Liverpool FC | - | Wigan Athletic | 5:2 | ||
| 2nd (2nd leg) | Wigan Athletic | - | Liverpool FC | 0:3 | ||
| 1st(1st leg): 19/09/1989 | 2nd (2nd leg): 04/10/1989 | Winner: Liverpool FC | ||||
| 1st(1st leg) | Mansfield Town | - | Luton Town | 3:4 | ||
| 2nd (2nd leg) | Luton Town | - | Mansfield Town | 7:2 | ||
| 1st(1st leg): 19/09/1989 | 2nd (2nd leg): 03/10/1989 | Winner: Luton Town | ||||
| 1st(1st leg) | Oldham Athletic | - | Leeds United | 2:1 | ||
| 2nd (2nd leg) | Leeds United | - | Oldham Athletic | 1:2 | ||
| 1st(1st leg): 19/09/1989 | 2nd (2nd leg): 03/10/1989 | Winner: Oldham Athletic | ||||
| 1st(1st leg) | Reading FC | - | Newcastle United | 3:1 | ||
| 2nd (2nd leg) | Newcastle United | - | Reading FC | 4:0 | ||
| 1st(1st leg): 19/09/1989 | 2nd (2nd leg): 04/10/1989 | Winner: Newcastle United | ||||
| 1st(1st leg) | Shrewsbury Town | - | Swindon Town | 0:3 | ||
| 2nd (2nd leg) | Swindon Town | - | Shrewsbury Town | 3:1 | ||
| 1st(1st leg): 19/09/1989 | 2nd (2nd leg): 03/10/1989 | Winner: Swindon Town | ||||
| 1st(1st leg) | Stoke City | - | Millwall FC | 1:0 | ||
| 2nd (2nd leg) | Millwall FC | - | Stoke City | 2:0 aet | ||
| 1st(1st leg): 19/09/1989 | 2nd (2nd leg): 03/10/1989 | Winner: Millwall FC | ||||
| 1st(1st leg) | Sunderland AFC | - | Fulham FC | 1:1 | ||
| 2nd (2nd leg) | Fulham FC | - | Sunderland AFC | 0:3 | ||
| 1st(1st leg): 19/09/1989 | 2nd (2nd leg): 03/10/1989 | Winner: Sunderland AFC | ||||
| 1st(1st leg) | Aston Villa | - | Wolverhampton Wanderers | 2:1 | ||
| 2nd (2nd leg) | Wolverhampton Wanderers | - | Aston Villa | 1:1 | ||
| 1st(1st leg): 20/09/1989 | 2nd (2nd leg): 04/10/1989 | Winner: Aston Villa | ||||
| 1st(1st leg) | Charlton Athletic | - | Hereford United | 3:1 | ||
| 2nd (2nd leg) | Hereford United | - | Charlton Athletic | 0:1 | ||
| 1st(1st leg): 20/09/1989 | 2nd (2nd leg): 04/10/1989 | Winner: Charlton Athletic | ||||
| 1st(1st leg) | Exeter City | - | Blackburn Rovers | 3:0 | ||
| 2nd (2nd leg) | Blackburn Rovers | - | Exeter City | 2:1 | ||
| 1st(1st leg): 20/09/1989 | 2nd (2nd leg): 03/10/1989 | Winner: Exeter City | ||||
| 1st(1st leg) | Middlesbrough FC | - | Halifax Town | 4:0 | ||
| 2nd (2nd leg) | Halifax Town | - | Middlesbrough FC | 0:1 | ||
| 1st(1st leg): 20/09/1989 | 2nd (2nd leg): 03/10/1989 | Winner: Middlesbrough FC | ||||
| 1st(1st leg) | Norwich City | - | Rotherham United | 1:1 | ||
| 2nd (2nd leg) | Rotherham United | - | Norwich City | 0:2 | ||
| 1st(1st leg): 20/09/1989 | 2nd (2nd leg): 03/10/1989 | Winner: Norwich City | ||||
| 1st(1st leg) | Nottingham Forest | - | Huddersfield Town | 1:1 | ||
| 2nd (2nd leg) | Huddersfield Town | - | Nottingham Forest | 3:3 aet | ||
| 1st(1st leg): 20/09/1989 | 2nd (2nd leg): 03/10/1989 | Winner: Nottingham Forest | ||||
| 1st(1st leg) | Portsmouth FC | - | Manchester United | 2:3 | ||
| 2nd (2nd leg) | Manchester United | - | Portsmouth FC | 0:0 | ||
| 1st(1st leg): 20/09/1989 | 2nd (2nd leg): 03/10/1989 | Winner: Manchester United | ||||
| 1st(1st leg) | Queens Park Rangers | - | Stockport County | 2:1 | ||
| 2nd (2nd leg) | Stockport County | - | Queens Park Rangers | 0:0 | ||
| 1st(1st leg): 20/09/1989 | 2nd (2nd leg): 02/10/1989 | Winner: Queens Park Rangers | ||||
| 1st(1st leg) | Sheffield Wednesday | - | Aldershot FC | 0:0 | ||
| 2nd (2nd leg) | Aldershot FC | - | Sheffield Wednesday | 0:8 | ||
| 1st(1st leg): 20/09/1989 | 2nd (2nd leg): 03/10/1989 | Winner: Sheffield Wednesday | ||||
| 1st(1st leg) | Tottenham Hotspur | - | Southend United | 1:0 | ||
| 2nd (2nd leg) | Southend United | - | Tottenham Hotspur | 3:2 aet | ||
| 1st(1st leg): 20/09/1989 | 2nd (2nd leg): 04/10/1989 | Winner: Tottenham Hotspur | ||||
| 1st(1st leg) | West Bromwich Albion | - | Bradford City | 1:3 | ||
| 2nd (2nd leg) | Bradford City | - | West Bromwich Albion | 3:5 aet | ||
| 1st(1st leg): 20/09/1989 | 2nd (2nd leg): 04/10/1989 | Winner: West Bromwich Albion | ||||
| 1st(1st leg) | York City | - | Southampton FC | 0:1 | ||
| 2nd (2nd leg) | Southampton FC | - | York City | 2:0 | ||
| 1st(1st leg): 20/09/1989 | 2nd (2nd leg): 03/10/1989 | Winner: Southampton FC | ||||
