| 1. Journée | 07.08.1999 | Tranmere Rovers | - | Bolton Wanderers | 0:0 | ||||
| 2. Journée | 14.08.1999 | Bolton Wanderers | - | Queens Park Rangers | 2:1 |  |
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| 3. Journée | 21.08.1999 | Ipswich Town | - | Bolton Wanderers | 1:0 | ||||
| 4. Journée | 28.08.1999 | Bolton Wanderers | - | Manchester City | 0:1 | ||||
| 6. Journée | 05.09.1999 | Bolton Wanderers | - | Birmingham City | 3:3 | ||||
| 7. Journée | 11.09.1999 | Charlton Athletic | - | Bolton Wanderers | 2:1 |  |
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| 8. Journée | 18.09.1999 | Bolton Wanderers | - | Barnsley FC | 2:2 | ||||
| 12. Journée | 16.10.1999 | Bolton Wanderers | - | Huddersfield Town | 1:0 | ||||
| 13. Journée | 19.10.1999 | Bolton Wanderers | - | Crewe Alexandra | 2:2 | ||||
| 14. Journée | 24.10.1999 | Norwich City | - | Bolton Wanderers | 2:1 | ||||
| 15. Journée | 27.10.1999 | Nottingham Forest | - | Bolton Wanderers | 1:1 | ||||
| 17. Journée | 06.11.1999 | Bolton Wanderers | - | Crystal Palace | 2:0 |
Angleterre