| 3. Round | 20/12/1999 | Bolton Wanderers | - | Cardiff City | 1:0 | ||||
| 4. Round | 07/01/2000 | Grimsby Town | - | Bolton Wanderers | 0:2 | ||||
| Round of 16 | 28/01/2000 | Cambridge United | - | Bolton Wanderers | 1:3 |  |
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| Quarter-finals | 19/02/2000 | Bolton Wanderers | - | Charlton Athletic | 1:0 | ||||
| Semi-finals | 02/04/2000 | Bolton Wanderers | - | Aston Villa | 1:4 pso | |
England