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