| 12. Round | 08/11/1998 | Manchester United | - | Newcastle United | 0:0 | ||||
| 17. Round | 12/12/1998 | Blackburn Rovers | - | Newcastle United | 0:0 | ||||
| 18. Round | 19/12/1998 | Newcastle United | - | Leicester City | 1:0 | ||||
| 19. Round | 26/12/1998 | Newcastle United | - | Leeds United | 0:3 | ||||
| 20. Round | 28/12/1998 | Liverpool FC | - | Newcastle United | 4:2 | ||||
| 22. Round | 17/01/1999 | Charlton Athletic | - | Newcastle United | 2:2 |  |
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| 28. Round | 10/03/1999 | Nottingham Forest | - | Newcastle United | 1:2 | ||||
| 29. Round | 13/03/1999 | Newcastle United | - | Manchester United | 1:2 | |
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| 30. Round | 20/03/1999 | West Ham United | - | Newcastle United | 2:0 | ||||
| 32. Round | 05/04/1999 | Newcastle United | - | Tottenham Hotspur | 1:1 |
Greece