| 37. Round | 12/03/1999 | Wolverhampton Wanderers | - | Bristol City | 3:0 | ||||
| 35. Round | 22/03/1999 | Barnsley FC | - | Bristol City | 2:0 | ||||
| 40. Round | 02/04/1999 | Bristol City | - | Port Vale FC | 2:0 | ||||
| 41. Round | 04/04/1999 | Portsmouth FC | - | Bristol City | 0:1 | ||||
| 42. Round | 09/04/1999 | Bristol City | - | Grimsby Town | 4:1 | ||||
| 39. Round | 12/04/1999 | Bolton Wanderers | - | Bristol City | 1:0 | ||||
| 43. Round | 16/04/1999 | Stockport County | - | Bristol City | 2:2 | ||||
| 44. Round | 23/04/1999 | Bristol City | - | Birmingham City | 1:2 | ||||
| 34. Round | 26/04/1999 | Crewe Alexandra | - | Bristol City | 1:0 | ||||
| 45. Round | 30/04/1999 | Sheffield United | - | Bristol City | 3:1 | ||||
| 46. Round | 08/05/1999 | Bristol City | - | Norwich City | 1:0 |
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