| 3. Round | 07/01/1989 | West Ham United | - | Arsenal FC | 2:2 | ||||
| 3. Round | 10/01/1989 | Arsenal FC | - | West Ham United | 0:1 | ||||
| 4. Round | 28/01/1989 | Swindon Town | - | West Ham United | 0:0 | ||||
| 4. Round | 01/02/1989 | West Ham United | - | Swindon Town | 1:0 | ||||
| Round of 16 | 17/02/1989 | Charlton Athletic | - | West Ham United | 0:1 |
England