| 20. Round | 23/11/1999 | Fulham FC | - | Bolton Wanderers | 1:1 | ||||
| 21. Round | 27/11/1999 | Portsmouth FC | - | Bolton Wanderers | 0:0 | ||||
| 27. Round | 15/01/2000 | Queens Park Rangers | - | Bolton Wanderers | 0:1 | ||||
| 28. Round | 22/01/2000 | Bolton Wanderers | - | Ipswich Town | 1:1 | ||||
| 24. Round | 08/02/2000 | Port Vale FC | - | Bolton Wanderers | 0:1 | ||||
| 31. Round | 12/02/2000 | Birmingham City | - | Bolton Wanderers | 2:1 |  |
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| 35. Round | 07/03/2000 | Crystal Palace | - | Bolton Wanderers | 0:0 | ||||
| 37. Round | 18/03/2000 | Grimsby Town | - | Bolton Wanderers | 0:1 | |
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| 38. Round | 21/03/2000 | Bolton Wanderers | - | Sheffield United | 2:0 |  |
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| 39. Round | 25/03/2000 | Bolton Wanderers | - | Port Vale FC | 2:1 | ||||
| 29. Round | 05/04/2000 | Manchester City | - | Bolton Wanderers | 2:0 |
England