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| 1st(1st leg) | Bolton Wanderers | - | Tranmere Rovers | 0:1 (0:1) | ||
| 2nd (2nd leg) | Tranmere Rovers | - | Bolton Wanderers | 3:0 (2:0) | ||
| 1st(1st leg): 12/01/2000 | 2nd (2nd leg): 26/01/2000 | Winner: Tranmere Rovers | ||||
| 1st(1st leg) | Aston Villa | - | Leicester City | 0:0 (0:0) | ||
| 2nd (2nd leg) | Leicester City | - | Aston Villa | 1:0 (1:0) | ||
| 1st(1st leg): 25/01/2000 | 2nd (2nd leg): 02/02/2000 | Winner: Leicester City | ||||
