| 1. Round | 09/08/1999 | Darlington FC | - | Bolton Wanderers | 1:1 | ||||
| 2. Round | 20/09/1999 | Bolton Wanderers | - | Gillingham FC | 2:0 |  |
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| 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 |
Denmark