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 | ||||
4. Round | 28/08/1999 | Sheffield United | - | Ipswich Town | 2:2 | ||||
5. Round | 30/08/1999 | Ipswich Town | - | Barnsley FC | 6:1 | ||||
8. Round | 18/09/1999 | Ipswich Town | - | Birmingham City | 0:1 | ||||
9. Round | 26/09/1999 | Ipswich Town | - | Manchester City | 2:1 | ||||
10. Round | 02/10/1999 | Grimsby Town | - | Ipswich Town | 2:1 | ||||
12. Round | 16/10/1999 | Ipswich Town | - | Queens Park Rangers | 1:4 | ||||
6. Round | 02/11/1999 | Huddersfield Town | - | Ipswich Town | 3:1 | ||||
19. Round | 21/11/1999 | Norwich City | - | Ipswich Town | 0:0 | ||||
35. Round | 07/03/2000 | Ipswich Town | - | Blackburn Rovers | 0:0 | ||||
37. Round | 19/03/2000 | Ipswich Town | - | Norwich City | 0:2 | ||||
44. Round | 25/04/2000 | Ipswich Town | - | Crystal Palace | 1:0 | ||||
45. Round | 29/04/2000 | Charlton Athletic | - | Ipswich Town | 1:3 | ||||
46. Round | 07/05/2000 | Ipswich Town | - | Walsall FC | 2:0 |