| 2. Runde | 27.09.1988 | Sunderland AFC | - | West Ham United | 0:3 | ||||
| 2. Runde | 12.10.1988 | West Ham United | - | Sunderland AFC | 2:1 |  |
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| 3. Runde | 01.11.1988 | West Ham United | - | Derby County | 5:0 | ||||
| Achtelfinale | 30.11.1988 | West Ham United | - | Liverpool FC | 4:1 | ||||
| Viertelfinale | 18.01.1989 | West Ham United | - | Aston Villa | 2:1 | ||||
| Halbfinale | 12.02.1989 | West Ham United | - | Luton Town | 0:3 |
England