| 6. Round | 04/09/1998 | Swindon Town | - | Bristol City | 3:2 | ||||
| 8. Round | 12/09/1998 | Bristol City | - | West Bromwich Albion | 1:3 | ||||
| 9. Round | 18/09/1998 | Ipswich Town | - | Bristol City | 3:1 | ||||
| 10. Round | 25/09/1998 | Bristol City | - | Crewe Alexandra | 5:2 | ||||
| 11. Round | 28/09/1998 | Bristol City | - | Barnsley FC | 1:1 | ||||
| 12. Round | 02/10/1998 | Bury FC | - | Bristol City | 0:1 |  |
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| 13. Round | 09/10/1998 | Bristol City | - | Portsmouth FC | 2:2 | ||||
| 14. Round | 16/10/1998 | Port Vale FC | - | Bristol City | 3:2 | ||||
| 18. Round | 06/11/1998 | Bristol City | - | Wolverhampton Wanderers | 1:6 | |
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| 44. Round | 23/04/1999 | Bristol City | - | Birmingham City | 1:2 | ||||
| 34. Round | 26/04/1999 | Crewe Alexandra | - | Bristol City | 1:0 |
Scotland