| 3. Runde | 06.01.1990 | Sheffield United | - | AFC Bournemouth | 2:0 | ||||
| 4. Runde | 27.01.1990 | Sheffield United | - | Watford FC | 1:1 | ||||
| 4. Runde | 30.01.1990 | Watford FC | - | Sheffield United | 1:2 | ||||
| Achtelfinale | 18.02.1990 | Sheffield United | - | Barnsley FC | 2:2 | ||||
| Achtelfinale | 21.02.1990 | Barnsley FC | - | Sheffield United | 0:0 n.V. |
England