| 18. Round | 14/11/1999 | Sheffield United | - | Bolton Wanderers | 1:2 |  |
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| 21. Round | 27/11/1999 | Portsmouth FC | - | Bolton Wanderers | 0:0 | ||||
| 22. Round | 04/12/1999 | Bolton Wanderers | - | Tranmere Rovers | 2:3 | ||||
| 5. Round | 07/12/1999 | Blackburn Rovers | - | Bolton Wanderers | 3:1 | ||||
| 23. Round | 18/12/1999 | Bolton Wanderers | - | Stockport County | 0:1 | ||||
| 25. Round | 28/12/1999 | Bolton Wanderers | - | West Bromwich Albion | 1:1 | ||||
| 26. Round | 03/01/2000 | Walsall FC | - | Bolton Wanderers | 2:0 | ||||
| 24. Round | 08/02/2000 | Port Vale FC | - | Bolton Wanderers | 0:1 | ||||
| 31. Round | 12/02/2000 | Birmingham City | - | Bolton Wanderers | 2:1 | ||||
| 43. Round | 22/04/2000 | Huddersfield Town | - | Bolton Wanderers | 0:3 | ||||
| 45. Round | 29/04/2000 | Crewe Alexandra | - | Bolton Wanderers | 1:3 |
Ireland