| 3. Round | 05/01/1990 | Leicester City | - | Barnsley FC | 1:2 |  |
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| 4. Round | 27/01/1990 | Barnsley FC | - | Ipswich Town | 2:0 | ||||
| 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 | ||||
| Round of 16 | 04/03/1990 | Barnsley FC | - | Sheffield United | 0:1 |
Wales