| 26. Round | 03/01/2000 | Walsall FC | - | Bolton Wanderers | 2:0 |  |
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| 31. Round | 12/02/2000 | Birmingham City | - | Bolton Wanderers | 2:1 |  |
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| 32. Round | 22/02/2000 | Bolton Wanderers | - | Portsmouth FC | 3:0 | ||||
| 34. Round | 04/03/2000 | Bolton Wanderers | - | Charlton Athletic | 0:2 | |
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| 35. Round | 07/03/2000 | Crystal Palace | - | Bolton Wanderers | 0:0 | ||||
| 36. Round | 11/03/2000 | Bolton Wanderers | - | Fulham FC | 3:1 | ||||
| 40. Round | 14/03/2000 | Stockport County | - | Bolton Wanderers | 0:0 | ||||
| 37. Round | 18/03/2000 | Grimsby Town | - | Bolton Wanderers | 0:1 | ||||
| 38. Round | 21/03/2000 | Bolton Wanderers | - | Sheffield United | 2:0 | ||||
| 39. Round | 25/03/2000 | Bolton Wanderers | - | Port Vale FC | 2:1 | |
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| 43. Round | 22/04/2000 | Huddersfield Town | - | Bolton Wanderers | 0:3 | ||||
| 45. Round | 29/04/2000 | Crewe Alexandra | - | Bolton Wanderers | 1:3 | |
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| 44. Round | 03/05/2000 | Bolton Wanderers | - | Wolverhampton Wanderers | 2:1 | ||||
| 46. Round | 07/05/2000 | Bolton Wanderers | - | Norwich City | 1:0 |
Scotland