| 28. Round | 22/01/2000 | Sheffield United | - | Manchester City | 1:0 | ||||
| 30. Round | 05/02/2000 | Sheffield United | - | Tranmere Rovers | 3:1 | ||||
| 31. Round | 12/02/2000 | Crystal Palace | - | Sheffield United | 1:1 | ||||
| 32. Round | 19/02/2000 | Sheffield United | - | West Bromwich Albion | 6:0 |  |
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| 33. Round | 26/02/2000 | Charlton Athletic | - | Sheffield United | 1:0 | ||||
| 34. Round | 05/03/2000 | Sheffield United | - | Queens Park Rangers | 1:1 | |
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| 35. Round | 07/03/2000 | Sheffield United | - | Barnsley FC | 3:3 | |
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| 36. Round | 11/03/2000 | Port Vale FC | - | Sheffield United | 2:3 | ||||
| 37. Round | 18/03/2000 | Sheffield United | - | Stockport County | 1:0 | ||||
| 38. Round | 21/03/2000 | Bolton Wanderers | - | Sheffield United | 2:0 |
Scotland