| 1. Round | 08/08/1999 | Manchester City | - | Wolverhampton Wanderers | 0:1 | ||||
| 2. Round | 14/08/1999 | Fulham FC | - | Manchester City | 0:0 |  |
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| 3. Round | 21/08/1999 | Manchester City | - | Sheffield United | 6:0 |  |
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| 5. Round | 30/08/1999 | Manchester City | - | Nottingham Forest | 1:0 | ||||
| 7. Round | 11/09/1999 | Manchester City | - | Crystal Palace | 2:1 | ||||
| 6. Round | 28/09/1999 | Norwich City | - | Manchester City | 1:0 | ||||
| 10. Round | 02/10/1999 | Manchester City | - | Port Vale FC | 2:1 | |
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| 12. Round | 16/10/1999 | Tranmere Rovers | - | Manchester City | 1:1 | ||||
| 13. Round | 19/10/1999 | Birmingham City | - | Manchester City | 0:1 | ||||
| 14. Round | 23/10/1999 | Manchester City | - | Blackburn Rovers | 2:0 | ||||
| 15. Round | 27/10/1999 | Manchester City | - | Ipswich Town | 1:0 | ||||
| 16. Round | 30/10/1999 | Port Vale FC | - | Manchester City | 1:2 |
Scotland