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| H (Match allé) | AFC Bournemouth | - | Wolverhampton Wanderers | 1:1 (1:0) | ||
| R (match retour) | Wolverhampton Wanderers | - | AFC Bournemouth | 1:2 (0:1) | ||
| H (Match allé): 15.09.1998 | R (match retour): 22.09.1998 | vainqueur: AFC Bournemouth | ||||
| H (Match allé) | Barnsley FC | - | Reading FC | 3:0 (1:0) | ||
| R (match retour) | Reading FC | - | Barnsley FC | 1:1 (0:0) | ||
| H (Match allé): 15.09.1998 | R (match retour): 23.09.1998 | vainqueur: Barnsley FC | ||||
| H (Match allé) | Blackpool FC | - | Tranmere Rovers | 2:1 (1:1) | ||
| R (match retour) | Tranmere Rovers | - | Blackpool FC | 3:1 (1:1) | ||
| H (Match allé): 15.09.1998 | R (match retour): 22.09.1998 | vainqueur: Tranmere Rovers | ||||
| H (Match allé) | Bolton Wanderers | - | Hull City | 3:1 (1:0) | ||
| R (match retour) | Hull City | - | Bolton Wanderers | 2:3 (1:1) | ||
| H (Match allé): 15.09.1998 | R (match retour): 22.09.1998 | vainqueur: Bolton Wanderers | ||||
| H (Match allé) | Brentford FC | - | Tottenham Hotspur | 2:3 (1:1) | ||
| R (match retour) | Tottenham Hotspur | - | Brentford FC | 3:2 (1:1) | ||
| H (Match allé): 15.09.1998 | R (match retour): 23.09.1998 | vainqueur: Tottenham Hotspur | ||||
| H (Match allé) | Bury FC | - | Crystal Palace | 3:0 (2:0) | ||
| R (match retour) | Crystal Palace | - | Bury FC | 2:1 (1:1) | ||
| H (Match allé): 15.09.1998 | R (match retour): 23.09.1998 | vainqueur: Bury FC | ||||
| H (Match allé) | Fulham FC | - | Southampton FC | 1:1 (0:0) | ||
| R (match retour) | Southampton FC | - | Fulham FC | 0:1 (0:1) | ||
| H (Match allé): 15.09.1998 | R (match retour): 23.09.1998 | vainqueur: Fulham FC | ||||
| H (Match allé) | Halifax Town | - | Bradford City | 1:2 (0:1) | ||
| R (match retour) | Bradford City | - | Halifax Town | 3:1 (0:0) | ||
| H (Match allé): 15.09.1998 | R (match retour): 22.09.1998 | vainqueur: Bradford City | ||||
| H (Match allé) | Huddersfield Town | - | Everton FC | 1:1 (1:1) | ||
| R (match retour) | Everton FC | - | Huddersfield Town | 2:1 (2:1) | ||
| H (Match allé): 15.09.1998 | R (match retour): 23.09.1998 | vainqueur: Everton FC | ||||
| H (Match allé) | Ipswich Town | - | Luton Town | 2:1 (0:0) | ||
| R (match retour) | Luton Town | - | Ipswich Town | 4:2 (0:1, 2:1) ap | ||
| H (Match allé): 15.09.1998 | R (match retour): 22.09.1998 | vainqueur: Luton Town | ||||
| H (Match allé) | Leyton Orient | - | Nottingham Forest | 1:5 (0:4) | ||
| R (match retour) | Nottingham Forest | - | Leyton Orient | 0:0 (0:0) | ||
| H (Match allé): 15.09.1998 | R (match retour): 22.09.1998 | vainqueur: Nottingham Forest | ||||
| H (Match allé) | Macclesfield Town | - | Birmingham City | 0:3 (0:0) | ||
| R (match retour) | Birmingham City | - | Macclesfield Town | 6:0 (3:0) | ||
| H (Match allé): 15.09.1998 | R (match retour): 22.09.1998 | vainqueur: Birmingham City | ||||
| H (Match allé) | Northampton Town | - | West Ham United | 2:0 (0:0) | ||
| R (match retour) | West Ham United | - | Northampton Town | 1:0 (0:0) | ||
| H (Match allé): 15.09.1998 | R (match retour): 22.09.1998 | vainqueur: Northampton Town | ||||
| H (Match allé) | Portsmouth FC | - | Wimbledon FC | 2:1 (2:1) | ||
| R (match retour) | Wimbledon FC | - | Portsmouth FC | 4:1 (1:1, 2:1) ap | ||
| H (Match allé): 15.09.1998 | R (match retour): 22.09.1998 | vainqueur: Wimbledon FC | ||||
| H (Match allé) | Sheffield United | - | Grimsby Town | 2:1 (1:0) | ||
| R (match retour) | Grimsby Town | - | Sheffield United | 2:0 (0:0, 1:0) ap | ||
| H (Match allé): 15.09.1998 | R (match retour): 22.09.1998 | vainqueur: Grimsby Town | ||||
| H (Match allé) | Sunderland AFC | - | Chester City | 3:0 (2:0) | ||
| R (match retour) | Chester City | - | Sunderland AFC | 0:1 (0:1) | ||
| H (Match allé): 15.09.1998 | R (match retour): 22.09.1998 | vainqueur: Sunderland AFC | ||||
| H (Match allé) | Bristol City | - | Crewe Alexandra | 1:1 (1:1) | ||
| R (match retour) | Crewe Alexandra | - | Bristol City | 2:0 (0:0) | ||
| H (Match allé): 16.09.1998 | R (match retour): 22.09.1998 | vainqueur: Crewe Alexandra | ||||
| H (Match allé) | Coventry City | - | Southend United | 1:0 (0:0) | ||
| R (match retour) | Southend United | - | Coventry City | 0:4 (0:3) | ||
| H (Match allé): 16.09.1998 | R (match retour): 22.09.1998 | vainqueur: Coventry City | ||||
| H (Match allé) | Derby County | - | Manchester City | 1:1 (1:1) | ||
| R (match retour) | Manchester City | - | Derby County | 0:1 (0:1) | ||
| H (Match allé): 16.09.1998 | R (match retour): 23.09.1998 | vainqueur: Derby County | ||||
| H (Match allé) | Leicester City | - | Chesterfield FC | 3:0 (1:0) | ||
| R (match retour) | Chesterfield FC | - | Leicester City | 1:3 (1:0) | ||
| H (Match allé): 16.09.1998 | R (match retour): 22.09.1998 | vainqueur: Leicester City | ||||
| H (Match allé) | Middlesbrough FC | - | Wycombe Wanderers | 2:0 (1:0) | ||
| R (match retour) | Wycombe Wanderers | - | Middlesbrough FC | 1:1 (1:0) | ||
| H (Match allé): 16.09.1998 | R (match retour): 22.09.1998 | vainqueur: Middlesbrough FC | ||||
| H (Match allé) | Norwich City | - | Wigan Athletic | 1:0 (1:0) | ||
| R (match retour) | Wigan Athletic | - | Norwich City | 2:3 (0:2) | ||
| H (Match allé): 16.09.1998 | R (match retour): 22.09.1998 | vainqueur: Norwich City | ||||
| H (Match allé) | Queens Park Rangers | - | Charlton Athletic | 0:2 (0:2) | ||
| R (match retour) | Charlton Athletic | - | Queens Park Rangers | 1:0 (1:0) | ||
| H (Match allé): 16.09.1998 | R (match retour): 22.09.1998 | vainqueur: Charlton Athletic | ||||
| H (Match allé) | Sheffield Wednesday | - | Cambridge United | 0:1 (0:1) | ||
| R (match retour) | Cambridge United | - | Sheffield Wednesday | 1:1 (0:0) | ||
| H (Match allé): 16.09.1998 | R (match retour): 22.09.1998 | vainqueur: Cambridge United | ||||
