2. Round | 13/09/1999 | Tranmere Rovers | - | Coventry City | 5:1 | ||||
2. Round | 21/09/1999 | Coventry City | - | Tranmere Rovers | 3:1 | ||||
3. Round | 11/10/1999 | Tranmere Rovers | - | Oxford United | 2:0 | ||||
Round of 16 | 29/11/1999 | Tranmere Rovers | - | Barnsley FC | 4:0 | ||||
Quarter-finals | 13/12/1999 | Tranmere Rovers | - | Middlesbrough FC | 2:1 | ||||
Semi-finals | 11/01/2000 | Bolton Wanderers | - | Tranmere Rovers | 0:1 | ||||
Final | 26/02/2000 | Leicester City | - | Tranmere Rovers | 2:1 |