2. Round | 13/09/1999 | Gillingham FC | - | Bolton Wanderers | 1:4 | ||||
2. Round | 20/09/1999 | Bolton Wanderers | - | Gillingham FC | 2:0 | ||||
3. Round | 12/10/1999 | Derby County | - | Bolton Wanderers | 1:2 | ||||
Semi-finals | 25/01/2000 | Tranmere Rovers | - | Bolton Wanderers | 3:0 |