1. Round | 09/08/1999 | Darlington FC | - | Bolton Wanderers | 1:1 | ||||
1. Round | 23/08/1999 | Bolton Wanderers | - | Darlington FC | 5:3 | ||||
2. Round | 20/09/1999 | Bolton Wanderers | - | Gillingham FC | 2:0 | ||||
Round of 16 | 29/11/1999 | Bolton Wanderers | - | Sheffield Wednesday | 1:0 | ||||
Quarter-finals | 13/12/1999 | Bolton Wanderers | - | Wimbledon FC | 2:1 |