| 1. Round | 07/08/1999 | Tranmere Rovers | - | Bolton Wanderers | 0:0 |  |
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| 2. Round | 14/08/1999 | Bolton Wanderers | - | Queens Park Rangers | 2:1 | ||||
| 3. Round | 21/08/1999 | Ipswich Town | - | Bolton Wanderers | 1:0 | ||||
| 4. Round | 28/08/1999 | Bolton Wanderers | - | Manchester City | 0:1 | ||||
| 6. Round | 05/09/1999 | Bolton Wanderers | - | Birmingham City | 3:3 |  |
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| 7. Round | 11/09/1999 | Charlton Athletic | - | Bolton Wanderers | 2:1 | ||||
| 8. Round | 18/09/1999 | Bolton Wanderers | - | Barnsley FC | 2:2 |
Denmark