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| U | Port Vale FC | - | Wimbledon FC | 1:2 | ||
| R | Wimbledon FC | - | Port Vale FC | 3:0 | ||
| U: 18.09.1989 | R: 04.10.1989 | Winnaars: Wimbledon FC | ||||
| U | Arsenal FC | - | Plymouth Argyle | 2:0 | ||
| R | Plymouth Argyle | - | Arsenal FC | 1:6 | ||
| U: 19.09.1989 | R: 03.10.1989 | Winnaars: Arsenal FC | ||||
| U | Barnsley FC | - | Blackpool FC | 1:1 | ||
| R | Blackpool FC | - | Barnsley FC | 5:4 d.p. | ||
| U: 19.09.1989 | R: 03.10.1989 | Winnaars: Blackpool FC | ||||
| U | Birmingham City | - | West Ham United | 1:2 | ||
| R | West Ham United | - | Birmingham City | 1:1 | ||
| U: 19.09.1989 | R: 04.10.1989 | Winnaars: West Ham United | ||||
| U | Bolton Wanderers | - | Watford FC | 2:1 | ||
| R | Watford FC | - | Bolton Wanderers | 1:1 | ||
| U: 19.09.1989 | R: 03.10.1989 | Winnaars: Bolton Wanderers | ||||
| U | Brentford FC | - | Manchester City | 2:1 | ||
| R | Manchester City | - | Brentford FC | 4:1 | ||
| U: 19.09.1989 | R: 04.10.1989 | Winnaars: Manchester City | ||||
| U | Cambridge United | - | Derby County | 2:1 | ||
| R | Derby County | - | Cambridge United | 5:0 | ||
| U: 19.09.1989 | R: 04.10.1989 | Winnaars: Derby County | ||||
| U | Chelsea FC | - | Scarborough FC | 1:1 | ||
| R | Scarborough FC | - | Chelsea FC | 3:2 n.v. | ||
| U: 19.09.1989 | R: 04.10.1989 | Winnaars: Scarborough FC | ||||
| U | Crewe Alexandra | - | AFC Bournemouth | 0:1 | ||
| R | AFC Bournemouth | - | Crewe Alexandra | 0:0 | ||
| U: 19.09.1989 | R: 03.10.1989 | Winnaars: AFC Bournemouth | ||||
| U | Crystal Palace | - | Leicester City | 1:2 | ||
| R | Leicester City | - | Crystal Palace | 2:3 n.v. | ||
| U: 19.09.1989 | R: 04.10.1989 | Winnaars: Crystal Palace | ||||
| U | Grimsby Town | - | Coventry City | 3:1 | ||
| R | Coventry City | - | Grimsby Town | 3:0 | ||
| U: 19.09.1989 | R: 04.10.1989 | Winnaars: Coventry City | ||||
| U | Ipswich Town | - | Tranmere Rovers | 0:1 | ||
| R | Tranmere Rovers | - | Ipswich Town | 1:0 | ||
| U: 19.09.1989 | R: 03.10.1989 | Winnaars: Tranmere Rovers | ||||
| U | Leyton Orient | - | Everton FC | 0:2 | ||
| R | Everton FC | - | Leyton Orient | 2:2 | ||
| U: 19.09.1989 | R: 03.10.1989 | Winnaars: Everton FC | ||||
| U | Liverpool FC | - | Wigan Athletic | 5:2 | ||
| R | Wigan Athletic | - | Liverpool FC | 0:3 | ||
| U: 19.09.1989 | R: 04.10.1989 | Winnaars: Liverpool FC | ||||
| U | Mansfield Town | - | Luton Town | 3:4 | ||
| R | Luton Town | - | Mansfield Town | 7:2 | ||
| U: 19.09.1989 | R: 03.10.1989 | Winnaars: Luton Town | ||||
| U | Oldham Athletic | - | Leeds United | 2:1 | ||
| R | Leeds United | - | Oldham Athletic | 1:2 | ||
| U: 19.09.1989 | R: 03.10.1989 | Winnaars: Oldham Athletic | ||||
| U | Reading FC | - | Newcastle United | 3:1 | ||
| R | Newcastle United | - | Reading FC | 4:0 | ||
| U: 19.09.1989 | R: 04.10.1989 | Winnaars: Newcastle United | ||||
| U | Shrewsbury Town | - | Swindon Town | 0:3 | ||
| R | Swindon Town | - | Shrewsbury Town | 3:1 | ||
| U: 19.09.1989 | R: 03.10.1989 | Winnaars: Swindon Town | ||||
| U | Stoke City | - | Millwall FC | 1:0 | ||
| R | Millwall FC | - | Stoke City | 2:0 n.v. | ||
| U: 19.09.1989 | R: 03.10.1989 | Winnaars: Millwall FC | ||||
| U | Sunderland AFC | - | Fulham FC | 1:1 | ||
| R | Fulham FC | - | Sunderland AFC | 0:3 | ||
| U: 19.09.1989 | R: 03.10.1989 | Winnaars: Sunderland AFC | ||||
| U | Aston Villa | - | Wolverhampton Wanderers | 2:1 | ||
| R | Wolverhampton Wanderers | - | Aston Villa | 1:1 | ||
| U: 20.09.1989 | R: 04.10.1989 | Winnaars: Aston Villa | ||||
| U | Charlton Athletic | - | Hereford United | 3:1 | ||
| R | Hereford United | - | Charlton Athletic | 0:1 | ||
| U: 20.09.1989 | R: 04.10.1989 | Winnaars: Charlton Athletic | ||||
| U | Exeter City | - | Blackburn Rovers | 3:0 | ||
| R | Blackburn Rovers | - | Exeter City | 2:1 | ||
| U: 20.09.1989 | R: 03.10.1989 | Winnaars: Exeter City | ||||
| U | Middlesbrough FC | - | Halifax Town | 4:0 | ||
| R | Halifax Town | - | Middlesbrough FC | 0:1 | ||
| U: 20.09.1989 | R: 03.10.1989 | Winnaars: Middlesbrough FC | ||||
| U | Norwich City | - | Rotherham United | 1:1 | ||
| R | Rotherham United | - | Norwich City | 0:2 | ||
| U: 20.09.1989 | R: 03.10.1989 | Winnaars: Norwich City | ||||
| U | Nottingham Forest | - | Huddersfield Town | 1:1 | ||
| R | Huddersfield Town | - | Nottingham Forest | 3:3 n.v. | ||
| U: 20.09.1989 | R: 03.10.1989 | Winnaars: Nottingham Forest | ||||
| U | Portsmouth FC | - | Manchester United | 2:3 | ||
| R | Manchester United | - | Portsmouth FC | 0:0 | ||
| U: 20.09.1989 | R: 03.10.1989 | Winnaars: Manchester United | ||||
| U | Queens Park Rangers | - | Stockport County | 2:1 | ||
| R | Stockport County | - | Queens Park Rangers | 0:0 | ||
| U: 20.09.1989 | R: 02.10.1989 | Winnaars: Queens Park Rangers | ||||
| U | Sheffield Wednesday | - | Aldershot FC | 0:0 | ||
| R | Aldershot FC | - | Sheffield Wednesday | 0:8 | ||
| U: 20.09.1989 | R: 03.10.1989 | Winnaars: Sheffield Wednesday | ||||
| U | Tottenham Hotspur | - | Southend United | 1:0 | ||
| R | Southend United | - | Tottenham Hotspur | 3:2 n.v. | ||
| U: 20.09.1989 | R: 04.10.1989 | Winnaars: Tottenham Hotspur | ||||
| U | West Bromwich Albion | - | Bradford City | 1:3 | ||
| R | Bradford City | - | West Bromwich Albion | 3:5 n.v. | ||
| U: 20.09.1989 | R: 04.10.1989 | Winnaars: West Bromwich Albion | ||||
| U | York City | - | Southampton FC | 0:1 | ||
| R | Southampton FC | - | York City | 2:0 | ||
| U: 20.09.1989 | R: 03.10.1989 | Winnaars: Southampton FC | ||||
