| 5. Round | 30/08/1999 | Ipswich Town | - | Barnsley FC | 6:1 |  |
|||
| 6. Round | 03/09/1999 | Barnsley FC | - | Tranmere Rovers | 3:0 | |
|||
| 12. Round | 16/10/1999 | Barnsley FC | - | Wolverhampton Wanderers | 1:2 | ||||
| 17. Round | 06/11/1999 | Barnsley FC | - | Sheffield United | 2:0 | ||||
| 19. Round | 20/11/1999 | Barnsley FC | - | Birmingham City | 2:1 | ||||
| 20. Round | 24/11/1999 | Manchester City | - | Barnsley FC | 3:1 | ||||
| 24. Round | 26/12/1999 | Grimsby Town | - | Barnsley FC | 0:3 | ||||
| 11. Round | 08/01/2000 | Norwich City | - | Barnsley FC | 2:2 | ||||
| 27. Round | 15/01/2000 | Crystal Palace | - | Barnsley FC | 0:2 | ||||
| 32. Round | 19/02/2000 | Barnsley FC | - | Queens Park Rangers | 1:1 |
England