| 21. Round | 09/01/1999 | Newcastle United | - | Chelsea FC | 0:1 | ||||
| 22. Round | 17/01/1999 | Charlton Athletic | - | Newcastle United | 2:2 | ||||
| 23. Round | 30/01/1999 | Newcastle United | - | Aston Villa | 2:1 | ||||
| 25. Round | 17/02/1999 | Newcastle United | - | Coventry City | 4:1 | ||||
| 26. Round | 20/02/1999 | Southampton FC | - | Newcastle United | 2:1 |  |
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| 27. Round | 28/02/1999 | Newcastle United | - | Arsenal FC | 1:1 | ||||
| 28. Round | 10/03/1999 | Nottingham Forest | - | Newcastle United | 1:2 | ||||
| 29. Round | 13/03/1999 | Newcastle United | - | Manchester United | 1:2 | ||||
| 30. Round | 20/03/1999 | West Ham United | - | Newcastle United | 2:0 | ||||
| 31. Round | 03/04/1999 | Derby County | - | Newcastle United | 3:4 | ||||
| 32. Round | 05/04/1999 | Newcastle United | - | Tottenham Hotspur | 1:1 | ||||
| 35. Round | 24/04/1999 | Wimbledon FC | - | Newcastle United | 1:1 | ||||
| 36. Round | 01/05/1999 | Newcastle United | - | Middlesbrough FC | 1:1 | ||||
| 37. Round | 08/05/1999 | Leicester City | - | Newcastle United | 2:0 |
France