| 22. Round | 16/01/1999 | Tottenham Hotspur | - | Wimbledon FC | 0:0 | ||||
| 24. Round | 06/02/1999 | Tottenham Hotspur | - | Coventry City | 0:0 | ||||
| 26. Round | 20/02/1999 | Middlesbrough FC | - | Tottenham Hotspur | 0:0 | ||||
| 27. Round | 27/02/1999 | Tottenham Hotspur | - | Derby County | 1:1 | ||||
| 25. Round | 02/03/1999 | Tottenham Hotspur | - | Southampton FC | 3:0 | ||||
| 29. Round | 13/03/1999 | Tottenham Hotspur | - | Aston Villa | 1:0 | ||||
| 32. Round | 05/04/1999 | Newcastle United | - | Tottenham Hotspur | 1:1 | ||||
| 34. Round | 17/04/1999 | Nottingham Forest | - | Tottenham Hotspur | 0:1 | ||||
| 30. Round | 20/04/1999 | Charlton Athletic | - | Tottenham Hotspur | 1:4 | ||||
| 35. Round | 24/04/1999 | Tottenham Hotspur | - | West Ham United | 1:2 |  |
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| 36. Round | 01/05/1999 | Liverpool FC | - | Tottenham Hotspur | 3:2 |  |
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| 33. Round | 05/05/1999 | Tottenham Hotspur | - | Arsenal FC | 1:3 | ||||
| 37. Round | 10/05/1999 | Tottenham Hotspur | - | Chelsea FC | 2:2 |
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