| 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 | ||||
| 5. Round | 30/08/1999 | Ipswich Town | - | Barnsley FC | 6:1 | ||||
| 6. Round | 03/09/1999 | Barnsley FC | - | Tranmere Rovers | 3:0 | ||||
| 7. Round | 10/09/1999 | Barnsley FC | - | Stockport County | 2:1 | ||||
| 8. Round | 18/09/1999 | Bolton Wanderers | - | Barnsley FC | 2:2 | ||||
| 13. Round | 19/10/1999 | Barnsley FC | - | Swindon Town | 1:0 | ||||
| 14. Round | 23/10/1999 | Crewe Alexandra | - | Barnsley FC | 0:1 | ||||
| 15. Round | 26/10/1999 | Huddersfield Town | - | Barnsley FC | 2:1 | ||||
| 19. Round | 20/11/1999 | Barnsley FC | - | Birmingham City | 2:1 | ||||
| 27. Round | 15/01/2000 | Crystal Palace | - | Barnsley FC | 0:2 |  |
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| 28. Round | 22/01/2000 | Barnsley FC | - | Blackburn Rovers | 5:1 |
England