| 2. Jornada | 22.08.1998 | Tottenham Hotspur | - | Sheffield Wednesday | 0:3 | ||||
| 6. Jornada | 19.09.1998 | Southampton | - | Tottenham Hotspur | 1:1 | ||||
| 7. Jornada | 26.09.1998 | Tottenham Hotspur | - | Leeds United | 3:3 | ||||
| 9. Jornada | 19.10.1998 | Leicester City | - | Tottenham Hotspur | 2:1 | ||||
| 27. Jornada | 27.02.1999 | Tottenham Hotspur | - | Derby County | 1:1 | ||||
| 25. Jornada | 02.03.1999 | Tottenham Hotspur | - | Southampton | 3:0 |  |
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| 29. Jornada | 13.03.1999 | Tottenham Hotspur | - | Aston Villa | 1:0 | ||||
| 30. Jornada | 20.04.1999 | Charlton Athletic | - | Tottenham Hotspur | 1:4 | |
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| 35. Jornada | 24.04.1999 | Tottenham Hotspur | - | West Ham United | 1:2 | ||||
| 36. Jornada | 01.05.1999 | Liverpool | - | Tottenham Hotspur | 3:2 | ||||
| 33. Jornada | 05.05.1999 | Tottenham Hotspur | - | Arsenal | 1:3 | ||||
| 37. Jornada | 10.05.1999 | Tottenham Hotspur | - | Chelsea | 2:2 | ||||
| 38. Jornada | 16.05.1999 | Manchester United | - | Tottenham Hotspur | 2:1 |
Portugal