1. Round | 09/08/1999 | Blackpool FC | - | Tranmere Rovers | 2:1 | ||||
1. Round | 23/08/1999 | Tranmere Rovers | - | Blackpool FC | 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 | ||||
Semi-finals | 25/01/2000 | Tranmere Rovers | - | Bolton Wanderers | 3:0 |