30. Ronde | 20.03.1999 | Nottingham Forest | - | Middlesbrough FC | 1:2 | ||||
33. Ronde | 10.04.1999 | Middlesbrough FC | - | Charlton Athletic | 2:0 | ||||
34. Ronde | 17.04.1999 | Coventry City | - | Middlesbrough FC | 1:2 | ||||
35. Ronde | 24.04.1999 | Middlesbrough FC | - | Arsenal FC | 1:6 | ||||
36. Ronde | 01.05.1999 | Newcastle United | - | Middlesbrough FC | 1:1 | ||||
38. Ronde | 16.05.1999 | West Ham United | - | Middlesbrough FC | 4:0 |