| 5. Round | 24/08/1968 | Ipswich Town | - | Arsenal FC | 1:2 | ||||
| 6. Round | 27/08/1968 | Ipswich Town | - | Queens Park Rangers | 3:0 | ||||
| 7. Round | 31/08/1968 | Manchester City | - | Ipswich Town | 1:1 | ||||
| 13. Round | 08/10/1968 | Queens Park Rangers | - | Ipswich Town | 2:1 | ||||
| 18. Round | 09/11/1968 | Ipswich Town | - | Everton FC | 2:2 | ||||
| 20. Round | 23/11/1968 | Ipswich Town | - | West Ham United | 2:2 | ||||
| 21. Round | 30/11/1968 | Coventry City | - | Ipswich Town | 0:2 |  |
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| 24. Round | 21/12/1968 | Ipswich Town | - | Nottingham Forest | 2:3 | ||||
| 25. Round | 26/12/1968 | Ipswich Town | - | Chelsea FC | 1:3 | |
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| 34. Round | 18/02/1969 | Arsenal FC | - | Ipswich Town | 0:2 | ||||
| 31. Round | 23/04/1969 | West Bromwich Albion | - | Ipswich Town | 2:2 |
England