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| H | Bolton Wanderers | - | Tranmere Rovers | 0:1 (0:1) | ||
| R | Tranmere Rovers | - | Bolton Wanderers | 3:0 (2:0) | ||
| H: 12.01.2000 | R: 26.01.2000 | Sieger: Tranmere Rovers | ||||
| H | Aston Villa | - | Leicester City | 0:0 (0:0) | ||
| R | Leicester City | - | Aston Villa | 1:0 (1:0) | ||
| H: 25.01.2000 | R: 02.02.2000 | Sieger: Leicester City | ||||
