| 9. Jornada | 19.09.1998 | Barnsley FC | - | Crystal Palace | 4:0 | ||||
| 12. Jornada | 03.10.1998 | Barnsley FC | - | Bolton Wanderers | 2:2 | ||||
| 13. Jornada | 11.10.1998 | Barnsley FC | - | Port Vale FC | 0:2 | ||||
| 14. Jornada | 17.10.1998 | Sheffield United | - | Barnsley FC | 1:1 | ||||
| 15. Jornada | 20.10.1998 | Tranmere Rovers | - | Barnsley FC | 3:0 | ||||
| 20. Jornada | 21.11.1998 | Sunderland | - | Barnsley FC | 2:3 | ||||
| 21. Jornada | 27.11.1998 | Barnsley FC | - | Huddersfield Town | 7:1 | ||||
| 24. Jornada | 19.12.1998 | Barnsley FC | - | Swindon Town | 1:3 | ||||
| 29. Jornada | 30.01.1999 | Oxford United | - | Barnsley FC | 1:0 |
Trinidad y Tobago