| 31. Ronde | 03.04.1999 | Blackburn Rovers | - | Middlesbrough FC | 0:0 | ||||
| 32. Ronde | 05.04.1999 | Middlesbrough FC | - | Wimbledon FC | 3:1 | ||||
| 33. Ronde | 10.04.1999 | Middlesbrough FC | - | Charlton Athletic | 2:0 | ||||
| 28. Ronde | 14.04.1999 | Middlesbrough FC | - | Chelsea FC | 0:0 |  |
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| 34. Ronde | 17.04.1999 | Coventry City | - | Middlesbrough FC | 1:2 | |
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| 38. Ronde | 16.05.1999 | West Ham United | - | Middlesbrough FC | 4:0 |
Ierland