1. Round | 07/08/1999 | Ipswich Town | - | Nottingham Forest | 3:1 | ||||
2. Round | 15/08/1999 | Swindon Town | - | Ipswich Town | 1:4 | ||||
3. Round | 21/08/1999 | Ipswich Town | - | Bolton Wanderers | 1:0 | ||||
7. Round | 11/09/1999 | Portsmouth FC | - | Ipswich Town | 1:1 | ||||
14. Round | 23/10/1999 | Walsall FC | - | Ipswich Town | 0:1 | ||||
15. Round | 27/10/1999 | Manchester City | - | Ipswich Town | 1:0 | ||||
16. Round | 30/10/1999 | Ipswich Town | - | Grimsby Town | 2:0 | ||||
17. Round | 06/11/1999 | Blackburn Rovers | - | Ipswich Town | 2:2 | ||||
18. Round | 12/11/1999 | Ipswich Town | - | Tranmere Rovers | 0:0 | ||||
11. Round | 08/12/1999 | Crystal Palace | - | Ipswich Town | 2:2 | ||||
23. Round | 18/12/1999 | Ipswich Town | - | West Bromwich Albion | 3:1 | ||||
26. Round | 03/01/2000 | Port Vale FC | - | Ipswich Town | 1:2 | ||||
27. Round | 15/01/2000 | Ipswich Town | - | Swindon Town | 3:0 | ||||
28. Round | 22/01/2000 | Bolton Wanderers | - | Ipswich Town | 1:1 | ||||
29. Round | 29/01/2000 | Ipswich Town | - | Sheffield United | 1:1 |