| 3. Round | 05/01/1990 | Sheffield United | - | AFC Bournemouth | 2:0 | ||||
| 4. Round | 26/01/1990 | Sheffield United | - | Watford FC | 1:1 | ||||
| 4. Round | 29/01/1990 | Watford FC | - | Sheffield United | 1:2 | ||||
| Round of 16 | 17/02/1990 | Sheffield United | - | Barnsley FC | 2:2 | ||||
| Round of 16 | 20/02/1990 | Barnsley FC | - | Sheffield United | 0:0 aet |
England