 |
 |
|
|
| H (Match allé) | Barnsley FC | - | Stockport County | 1:1 (1:1) | ||
| R (match retour) | Stockport County | - | Barnsley FC | 3:3 (2:0, 2:2) ap | ||
| H (Match allé): 14.09.1999 | R (match retour): 21.09.1999 | vainqueur: Barnsley FC | ||||
| H (Match allé) | Birmingham City | - | Bristol Rovers | 2:0 (0:0) | ||
| R (match retour) | Bristol Rovers | - | Birmingham City | 0:1 (0:0) | ||
| H (Match allé): 14.09.1999 | R (match retour): 21.09.1999 | vainqueur: Birmingham City | ||||
| H (Match allé) | Bradford City | - | Reading FC | 1:1 (1:0) | ||
| R (match retour) | Reading FC | - | Bradford City | 2:2 (1:0, 1:1) ap | ||
| H (Match allé): 14.09.1999 | R (match retour): 22.09.1999 | vainqueur: Bradford City | ||||
| H (Match allé) | Crystal Palace | - | Leicester City | 3:3 (1:2) | ||
| R (match retour) | Leicester City | - | Crystal Palace | 4:2 (1:0) | ||
| H (Match allé): 14.09.1999 | R (match retour): 22.09.1999 | vainqueur: Leicester City | ||||
| H (Match allé) | Cardiff City | - | Wimbledon FC | 1:1 (1:0) | ||
| R (match retour) | Wimbledon FC | - | Cardiff City | 3:1 (0:1) | ||
| H (Match allé): 14.09.1999 | R (match retour): 21.09.1999 | vainqueur: Wimbledon FC | ||||
| H (Match allé) | Charlton Athletic | - | AFC Bournemouth | 0:0 (0:0) | ||
| R (match retour) | AFC Bournemouth | - | Charlton Athletic | 3:1 (0:0, 0:0, 0:0) tab | ||
| H (Match allé): 14.09.1999 | R (match retour): 21.09.1999 | vainqueur: AFC Bournemouth | ||||
| H (Match allé) | Chester City | - | Aston Villa | 0:1 (0:0) | ||
| R (match retour) | Aston Villa | - | Chester City | 5:0 (2:0) | ||
| H (Match allé): 14.09.1999 | R (match retour): 21.09.1999 | vainqueur: Aston Villa | ||||
| H (Match allé) | Chesterfield FC | - | Middlesbrough FC | 0:0 (0:0) | ||
| R (match retour) | Middlesbrough FC | - | Chesterfield FC | 2:1 (1:0) | ||
| H (Match allé): 14.09.1999 | R (match retour): 21.09.1999 | vainqueur: Middlesbrough FC | ||||
| H (Match allé) | Crewe Alexandra | - | Ipswich Town | 2:1 (0:1) | ||
| R (match retour) | Ipswich Town | - | Crewe Alexandra | 1:1 (1:0) | ||
| H (Match allé): 14.09.1999 | R (match retour): 21.09.1999 | vainqueur: Crewe Alexandra | ||||
| H (Match allé) | Gillingham FC | - | Bolton Wanderers | 1:4 (0:2) | ||
| R (match retour) | Bolton Wanderers | - | Gillingham FC | 2:0 (2:0) | ||
| H (Match allé): 14.09.1999 | R (match retour): 21.09.1999 | vainqueur: Bolton Wanderers | ||||
| H (Match allé) | Grimsby Town | - | Leyton Orient | 4:1 (2:1) | ||
| R (match retour) | Leyton Orient | - | Grimsby Town | 1:0 (1:0) | ||
| H (Match allé): 14.09.1999 | R (match retour): 21.09.1999 | vainqueur: Grimsby Town | ||||
| H (Match allé) | Huddersfield Town | - | Notts County | 2:1 (1:1) | ||
| R (match retour) | Notts County | - | Huddersfield Town | 2:2 (2:2) | ||
| H (Match allé): 14.09.1999 | R (match retour): 21.09.1999 | vainqueur: Huddersfield Town | ||||
| H (Match allé) | Hull City | - | Liverpool FC | 1:5 (0:2) | ||
| R (match retour) | Liverpool FC | - | Hull City | 4:2 (1:0) | ||
| H (Match allé): 14.09.1999 | R (match retour): 21.09.1999 | vainqueur: Liverpool FC | ||||
| H (Match allé) | Norwich City | - | Fulham FC | 0:4 (0:1) | ||
| R (match retour) | Fulham FC | - | Norwich City | 2:0 (1:0) | ||
| H (Match allé): 14.09.1999 | R (match retour): 21.09.1999 | vainqueur: Fulham FC | ||||
| H (Match allé) | Oxford United | - | Everton FC | 1:1 (1:1) | ||
| R (match retour) | Everton FC | - | Oxford United | 0:1 (0:1) | ||
| H (Match allé): 14.09.1999 | R (match retour): 22.09.1999 | vainqueur: Oxford United | ||||
| H (Match allé) | Portsmouth FC | - | Blackburn Rovers | 0:3 (0:0) | ||
| R (match retour) | Blackburn Rovers | - | Portsmouth FC | 3:1 (0:1) | ||
| H (Match allé): 14.09.1999 | R (match retour): 22.09.1999 | vainqueur: Blackburn Rovers | ||||
| H (Match allé) | Sheffield United | - | Preston North End | 2:0 (2:0) | ||
| R (match retour) | Preston North End | - | Sheffield United | 3:0 (1:0) | ||
| H (Match allé): 14.09.1999 | R (match retour): 21.09.1999 | vainqueur: Preston North End | ||||
| H (Match allé) | Stoke City | - | Sheffield Wednesday | 0:0 (0:0) | ||
| R (match retour) | Sheffield Wednesday | - | Stoke City | 3:1 (2:0) | ||
| H (Match allé): 14.09.1999 | R (match retour): 22.09.1999 | vainqueur: Sheffield Wednesday | ||||
| H (Match allé) | Sunderland AFC | - | Walsall FC | 3:2 (1:2) | ||
| R (match retour) | Walsall FC | - | Sunderland AFC | 0:5 (0:2) | ||
| H (Match allé): 14.09.1999 | R (match retour): 21.09.1999 | vainqueur: Sunderland AFC | ||||
| H (Match allé) | Swansea City | - | Derby County | 0:0 (0:0) | ||
| R (match retour) | Derby County | - | Swansea City | 3:1 (1:0) | ||
| H (Match allé): 14.09.1999 | R (match retour): 22.09.1999 | vainqueur: Derby County | ||||
| H (Match allé) | Tranmere Rovers | - | Coventry City | 5:1 (0:1) | ||
| R (match retour) | Coventry City | - | Tranmere Rovers | 3:1 (3:1) | ||
| H (Match allé): 14.09.1999 | R (match retour): 22.09.1999 | vainqueur: Tranmere Rovers | ||||
| H (Match allé) | Watford FC | - | Wigan Athletic | 2:0 (0:0) | ||
| R (match retour) | Wigan Athletic | - | Watford FC | 3:1 (1:0, 3:1) ap | ||
| H (Match allé): 14.09.1999 | R (match retour): 21.09.1999 | vainqueur: Watford FC | ||||
| H (Match allé) | West Bromwich Albion | - | Wycombe Wanderers | 1:1 (0:0) | ||
| R (match retour) | Wycombe Wanderers | - | West Bromwich Albion | 3:4 (1:2, 2:2) ap | ||
| H (Match allé): 14.09.1999 | R (match retour): 21.09.1999 | vainqueur: West Bromwich Albion | ||||
| H (Match allé) | Manchester City | - | Southampton FC | 0:0 (0:0) | ||
| R (match retour) | Southampton FC | - | Manchester City | 4:3 (2:1, 3:3) ap | ||
| H (Match allé): 15.09.1999 | R (match retour): 21.09.1999 | vainqueur: Southampton FC | ||||
| H (Match allé) | Nottingham Forest | - | Bristol City | 2:1 (1:1) | ||
| R (match retour) | Bristol City | - | Nottingham Forest | 0:0 (0:0) | ||
| H (Match allé): 15.09.1999 | R (match retour): 22.09.1999 | vainqueur: Nottingham Forest | ||||
