| 2. Jornada | 14.08.1999 | Sheffield United | - | Walsall FC | 1:1 |  |
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| 4. Jornada | 28.08.1999 | Sheffield United | - | Ipswich Town | 2:2 |  |
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| 5. Jornada | 30.08.1999 | Tranmere Rovers | - | Sheffield United | 1:3 | |
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| 6. Jornada | 04.09.1999 | Sheffield United | - | Crystal Palace | 3:1 | |
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| 8. Jornada | 18.09.1999 | Sheffield United | - | Charlton Athletic | 1:2 | ||||
| 9. Jornada | 25.09.1999 | Sheffield United | - | Wolverhampton Wanderers | 3:0 | ||||
| 10. Jornada | 02.10.1999 | Huddersfield Town | - | Sheffield United | 4:1 | ||||
| 11. Jornada | 09.10.1999 | Crewe Alexandra | - | Sheffield United | 1:0 | ||||
| 12. Jornada | 16.10.1999 | Sheffield United | - | Nottingham Forest | 2:1 | ||||
| 13. Jornada | 19.10.1999 | Sheffield United | - | Norwich City | 0:0 |
Brasil
Portugal