| 2. Round | 19/09/1989 | Ipswich Town | - | Tranmere Rovers | 0:1 | ||||
| 2. Round | 03/10/1989 | Tranmere Rovers | - | Ipswich Town | 1:0 |  |
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| 3. Round | 23/10/1989 | Tranmere Rovers | - | Millwall FC | 3:2 | ||||
| Round of 16 | 21/11/1989 | Tranmere Rovers | - | Tottenham Hotspur | 2:2 | ||||
| Round of 16 | 29/11/1989 | Tottenham Hotspur | - | Tranmere Rovers | 4:0 |
England