| 3. Round | 21/08/1999 | Manchester City | - | Sheffield United | 6:0 | ||||
| 15. Round | 26/10/1999 | Wolverhampton Wanderers | - | Sheffield United | 1:0 |  |
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| 19. Round | 20/11/1999 | Stockport County | - | Sheffield United | 1:1 | |
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| 20. Round | 23/11/1999 | Sheffield United | - | Port Vale FC | 1:3 | ||||
| 21. Round | 27/11/1999 | West Bromwich Albion | - | Sheffield United | 2:2 |  |
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| 7. Round | 30/11/1999 | Queens Park Rangers | - | Sheffield United | 3:1 | ||||
| 22. Round | 04/12/1999 | Sheffield United | - | Portsmouth FC | 1:0 | ||||
| 28. Round | 22/01/2000 | Sheffield United | - | Manchester City | 1:0 | ||||
| 31. Round | 12/02/2000 | Crystal Palace | - | Sheffield United | 1:1 | |
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| 32. Round | 19/02/2000 | Sheffield United | - | West Bromwich Albion | 6:0 | ||||
| 36. Round | 11/03/2000 | Port Vale FC | - | Sheffield United | 2:3 | ||||
| 37. Round | 18/03/2000 | Sheffield United | - | Stockport County | 1:0 | ||||
| 39. Round | 25/03/2000 | Sheffield United | - | Birmingham City | 1:2 | ||||
| 42. Round | 15/04/2000 | Fulham FC | - | Sheffield United | 4:0 | |
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| 45. Round | 29/04/2000 | Norwich City | - | Sheffield United | 2:1 |
Belgium