| 10. Round | 21/10/1989 | Tottenham Hotspur | - | Sheffield Wednesday | 3:0 |  |
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| 11. Round | 29/10/1989 | Liverpool FC | - | Tottenham Hotspur | 1:0 | ||||
| 24. Round | 03/02/1990 | Tottenham Hotspur | - | Norwich City | 4:0 | ||||
| 25. Round | 09/02/1990 | Chelsea FC | - | Tottenham Hotspur | 1:2 | ||||
| 26. Round | 20/02/1990 | Tottenham Hotspur | - | Aston Villa | 0:2 |
England