| 30. Round | 24/03/1989 | Aston Villa | - | West Ham United | 0:1 | ||||
| 31. Round | 26/03/1989 | West Ham United | - | Norwich City | 0:2 | ||||
| 32. Round | 31/03/1989 | Tottenham Hotspur | - | West Ham United | 3:0 | ||||
| 33. Round | 07/04/1989 | West Ham United | - | Derby County | 1:1 | ||||
| 24. Round | 10/04/1989 | West Ham United | - | Middlesbrough FC | 1:2 | ||||
| 29. Round | 14/04/1989 | West Ham United | - | Southampton FC | 1:2 | ||||
| 35. Round | 21/04/1989 | West Ham United | - | Millwall FC | 3:0 | ||||
| 25. Round | 02/05/1989 | Newcastle United | - | West Ham United | 1:2 | ||||
| 26. Round | 22/05/1989 | Liverpool FC | - | West Ham United | 5:1 |
Scotland