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| H (Match allé) | Bolton Wanderers | - | Tranmere Rovers | 0:1 (0:1) | ||
| R (match retour) | Tranmere Rovers | - | Bolton Wanderers | 3:0 (2:0) | ||
| H (Match allé): 12.01.2000 | R (match retour): 26.01.2000 | vainqueur: Tranmere Rovers | ||||
| H (Match allé) | Aston Villa | - | Leicester City | 0:0 (0:0) | ||
| R (match retour) | Leicester City | - | Aston Villa | 1:0 (1:0) | ||
| H (Match allé): 25.01.2000 | R (match retour): 02.02.2000 | vainqueur: Leicester City | ||||
