| 18. Ronde | 14.11.1999 | Sheffield United | - | Bolton Wanderers | 1:2 |  |
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| 21. Ronde | 27.11.1999 | Portsmouth FC | - | Bolton Wanderers | 0:0 | ||||
| 22. Ronde | 04.12.1999 | Bolton Wanderers | - | Tranmere Rovers | 2:3 | ||||
| 5. Ronde | 07.12.1999 | Blackburn Rovers | - | Bolton Wanderers | 3:1 | ||||
| 23. Ronde | 18.12.1999 | Bolton Wanderers | - | Stockport County | 0:1 | ||||
| 25. Ronde | 28.12.1999 | Bolton Wanderers | - | West Bromwich Albion | 1:1 | ||||
| 26. Ronde | 03.01.2000 | Walsall FC | - | Bolton Wanderers | 2:0 | ||||
| 24. Ronde | 08.02.2000 | Port Vale FC | - | Bolton Wanderers | 0:1 | ||||
| 31. Ronde | 12.02.2000 | Birmingham City | - | Bolton Wanderers | 2:1 | ||||
| 43. Ronde | 22.04.2000 | Huddersfield Town | - | Bolton Wanderers | 0:3 | ||||
| 45. Ronde | 29.04.2000 | Crewe Alexandra | - | Bolton Wanderers | 1:3 |
Ierland