| 3. Ronde | 21.08.1999 | Blackburn Rovers | - | Barnsley FC | 1:2 |  |
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| 4. Ronde | 28.08.1999 | Barnsley FC | - | Portsmouth FC | 6:0 | ||||
| 5. Ronde | 30.08.1999 | Ipswich Town | - | Barnsley FC | 6:1 | ||||
| 6. Ronde | 03.09.1999 | Barnsley FC | - | Tranmere Rovers | 3:0 | ||||
| 7. Ronde | 10.09.1999 | Barnsley FC | - | Stockport County | 2:1 | ||||
| 8. Ronde | 18.09.1999 | Bolton Wanderers | - | Barnsley FC | 2:2 | ||||
| 13. Ronde | 19.10.1999 | Barnsley FC | - | Swindon Town | 1:0 | ||||
| 14. Ronde | 23.10.1999 | Crewe Alexandra | - | Barnsley FC | 0:1 | ||||
| 15. Ronde | 26.10.1999 | Huddersfield Town | - | Barnsley FC | 2:1 | ||||
| 19. Ronde | 20.11.1999 | Barnsley FC | - | Birmingham City | 2:1 | ||||
| 27. Ronde | 15.01.2000 | Crystal Palace | - | Barnsley FC | 0:2 |  |
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| 28. Ronde | 22.01.2000 | Barnsley FC | - | Blackburn Rovers | 5:1 |
Engeland