| 2. Round | 18/09/1989 | Birmingham City | - | West Ham United | 1:2 | ||||
| 2. Round | 04/10/1989 | West Ham United | - | Birmingham City | 1:1 | ||||
| 3. Round | 25/10/1989 | Aston Villa | - | West Ham United | 0:0 | ||||
| 3. Round | 08/11/1989 | West Ham United | - | Aston Villa | 1:0 | ||||
| Round of 16 | 21/11/1989 | West Ham United | - | Wimbledon FC | 1:0 | ||||
| Quarter-finals | 16/01/1990 | West Ham United | - | Derby County | 1:1 | ||||
| Quarter-finals | 23/01/1990 | Derby County | - | West Ham United | 0:0 aet | ||||
| Quarter-finals | 30/01/1990 | West Ham United | - | Derby County | 2:1 | ||||
| Semi-finals | 13/02/1990 | Oldham Athletic | - | West Ham United | 6:0 | ||||
| Semi-finals | 06/03/1990 | West Ham United | - | Oldham Athletic | 3:0 |  |
England