| 6. Ronde | 03.09.1999 | Barnsley FC | - | Tranmere Rovers | 3:0 | ||||
| 7. Ronde | 11.09.1999 | Blackburn Rovers | - | Tranmere Rovers | 2:0 |  |
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| 8. Ronde | 18.09.1999 | Tranmere Rovers | - | Portsmouth FC | 2:4 | ||||
| 9. Ronde | 25.09.1999 | Tranmere Rovers | - | Charlton Athletic | 2:2 | ||||
| 10. Ronde | 03.10.1999 | Crewe Alexandra | - | Tranmere Rovers | 0:2 | ||||
| 11. Ronde | 09.10.1999 | Queens Park Rangers | - | Tranmere Rovers | 2:1 | ||||
| 12. Ronde | 16.10.1999 | Tranmere Rovers | - | Manchester City | 1:1 | ||||
| 14. Ronde | 23.10.1999 | Crystal Palace | - | Tranmere Rovers | 2:2 | ||||
| 17. Ronde | 06.11.1999 | Tranmere Rovers | - | West Bromwich Albion | 3:0 |
Engeland