| 32. Round | 20/02/1999 | Birmingham City | - | Bolton Wanderers | 0:0 | ||||
| 33. Round | 26/02/1999 | Bolton Wanderers | - | Crewe Alexandra | 1:3 | ||||
| 34. Round | 01/03/1999 | Huddersfield Town | - | Bolton Wanderers | 3:2 | ||||
| 36. Round | 08/03/1999 | Bolton Wanderers | - | Barnsley FC | 3:3 | ||||
| 40. Round | 02/04/1999 | Oxford United | - | Bolton Wanderers | 0:0 | ||||
| 43. Round | 16/04/1999 | Bolton Wanderers | - | Ipswich Town | 2:0 | ||||
| 45. Round | 29/04/1999 | Bolton Wanderers | - | Wolverhampton Wanderers | 1:1 | ||||
| 46. Round | 08/05/1999 | Portsmouth FC | - | Bolton Wanderers | 0:2 |
Denmark