| 25. Round | 20/02/1989 | Tottenham Hotspur | - | Norwich City | 2:1 | ||||
| 27. Round | 24/02/1989 | Southampton FC | - | Tottenham Hotspur | 0:2 |  |
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| 26. Round | 28/02/1989 | Tottenham Hotspur | - | Aston Villa | 2:0 | ||||
| 28. Round | 10/03/1989 | Derby County | - | Tottenham Hotspur | 1:1 | ||||
| 29. Round | 17/03/1989 | Coventry City | - | Tottenham Hotspur | 1:1 | ||||
| 33. Round | 21/03/1989 | Nottingham Forest | - | Tottenham Hotspur | 1:2 | ||||
| 30. Round | 25/03/1989 | Tottenham Hotspur | - | Liverpool FC | 1:2 | ||||
| 32. Round | 31/03/1989 | Tottenham Hotspur | - | West Ham United | 3:0 | |
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| 35. Round | 21/04/1989 | Tottenham Hotspur | - | Everton FC | 2:1 | ||||
| 36. Round | 28/04/1989 | Millwall FC | - | Tottenham Hotspur | 0:5 | ||||
| 38. Round | 12/05/1989 | Queens Park Rangers | - | Tottenham Hotspur | 1:0 |
Spain