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 | ||||
Final | 26/02/2000 | Leicester City | - | Tranmere Rovers | 2:1 |