| 1. Round | 09/08/1999 | Darlington FC | - | Bolton Wanderers | 1:1 |  |
|||
| 1. Round | 23/08/1999 | Bolton Wanderers | - | Darlington FC | 5:3 |  |
|||
| 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 | ||||
| Round of 16 | 29/11/1999 | Bolton Wanderers | - | Sheffield Wednesday | 1:0 | |
|||
| Quarter-finals | 13/12/1999 | Bolton Wanderers | - | Wimbledon FC | 2:1 | ||||
| Semi-finals | 11/01/2000 | Bolton Wanderers | - | Tranmere Rovers | 0:1 | ||||
| Semi-finals | 25/01/2000 | Tranmere Rovers | - | Bolton Wanderers | 3:0 |
Jamaica