| 1. Round | 12/08/2000 | Bolton Wanderers | - | Burnley FC | 1:1 | ||||
| 2. Round | 19/08/2000 | West Bromwich Albion | - | Bolton Wanderers | 0:2 |  |
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| 3. Round | 26/08/2000 | Bolton Wanderers | - | Preston North End | 2:0 | |
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| 4. Round | 28/08/2000 | Tranmere Rovers | - | Bolton Wanderers | 0:1 | ||||
| 6. Round | 09/09/2000 | Huddersfield Town | - | Bolton Wanderers | 2:3 | ||||
| 7. Round | 12/09/2000 | Grimsby Town | - | Bolton Wanderers | 0:1 | ||||
| 8. Round | 16/09/2000 | Bolton Wanderers | - | Portsmouth FC | 2:0 | ||||
| 9. Round | 23/09/2000 | Blackburn Rovers | - | Bolton Wanderers | 1:1 | ||||
| 10. Round | 30/09/2000 | Bolton Wanderers | - | Fulham FC | 0:2 | ||||
| 11. Round | 06/10/2000 | Gillingham FC | - | Bolton Wanderers | 2:2 | ||||
| 12. Round | 14/10/2000 | Bolton Wanderers | - | Wolverhampton Wanderers | 2:1 | ||||
| 13. Round | 17/10/2000 | Bolton Wanderers | - | Nottingham Forest | 0:0 | ||||
| 15. Round | 24/10/2000 | Watford FC | - | Bolton Wanderers | 1:0 | ||||
| 16. Round | 28/10/2000 | Bolton Wanderers | - | Crystal Palace | 3:3 | ||||
| 5. Round | 31/10/2000 | Bolton Wanderers | - | Queens Park Rangers | 3:1 | ||||
| 17. Round | 04/11/2000 | Birmingham City | - | Bolton Wanderers | 1:1 |
England