| 1. Round | 07/08/1999 | Charlton Athletic | - | Barnsley FC | 3:1 | ||||
| 2. Round | 14/08/1999 | Barnsley FC | - | Crystal Palace | 2:3 | ||||
| 3. Round | 21/08/1999 | Blackburn Rovers | - | Barnsley FC | 1:2 |  |
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| 4. Round | 28/08/1999 | Barnsley FC | - | Portsmouth FC | 6:0 | ||||
| 17. Round | 06/11/1999 | Barnsley FC | - | Sheffield United | 2:0 | ||||
| 46. Round | 07/05/2000 | Barnsley FC | - | Crewe Alexandra | 0:2 |
England