| 2. Round | 12/10/1988 | West Ham United | - | Sunderland AFC | 2:1 | ||||
| 3. Round | 31/10/1988 | West Ham United | - | Derby County | 5:0 | ||||
| Round of 16 | 30/11/1988 | West Ham United | - | Liverpool FC | 4:1 |  |
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| Quarter-finals | 18/01/1989 | West Ham United | - | Aston Villa | 2:1 | ||||
| Semi-finals | 12/02/1989 | West Ham United | - | Luton Town | 0:3 | ||||
| Semi-finals | 01/03/1989 | Luton Town | - | West Ham United | 2:0 |
England