| 7. Round | 11/09/1999 | Norwich City | - | Crewe Alexandra | 2:1 |  |
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| 8. Round | 18/09/1999 | Huddersfield Town | - | Norwich City | 1:0 |  |
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| 6. Round | 28/09/1999 | Norwich City | - | Manchester City | 1:0 | ||||
| 10. Round | 02/10/1999 | Norwich City | - | Fulham FC | 1:2 | ||||
| 12. Round | 16/10/1999 | Port Vale FC | - | Norwich City | 0:1 | ||||
| 13. Round | 19/10/1999 | Sheffield United | - | Norwich City | 0:0 | ||||
| 14. Round | 24/10/1999 | Norwich City | - | Bolton Wanderers | 2:1 | ||||
| 15. Round | 26/10/1999 | Norwich City | - | Stockport County | 2:0 | ||||
| 16. Round | 30/10/1999 | Fulham FC | - | Norwich City | 1:1 | ||||
| 17. Round | 06/11/1999 | Norwich City | - | Nottingham Forest | 1:0 | ||||
| 18. Round | 12/11/1999 | Swindon Town | - | Norwich City | 0:0 | ||||
| 21. Round | 28/11/1999 | Grimsby Town | - | Norwich City | 2:1 | ||||
| 22. Round | 04/12/1999 | Norwich City | - | West Bromwich Albion | 2:1 |
England