| 1. Round | 24/08/1990 | Tottenham Hotspur | - | Manchester City | 3:1 | ||||
| 2. Round | 27/08/1990 | Sunderland AFC | - | Tottenham Hotspur | 0:0 | ||||
| 3. Round | 31/08/1990 | Arsenal FC | - | Tottenham Hotspur | 0:0 | ||||
| 4. Round | 07/09/1990 | Tottenham Hotspur | - | Derby County | 3:0 | ||||
| 5. Round | 14/09/1990 | Leeds United | - | Tottenham Hotspur | 0:2 | ||||
| 6. Round | 21/09/1990 | Tottenham Hotspur | - | Crystal Palace | 1:1 | ||||
| 7. Round | 28/09/1990 | Tottenham Hotspur | - | Aston Villa | 2:1 | ||||
| 11. Round | 03/11/1990 | Tottenham Hotspur | - | Liverpool FC | 1:3 | ||||
| 20. Round | 28/12/1990 | Southampton FC | - | Tottenham Hotspur | 3:0 | ||||
| 27. Round | 22/02/1991 | Wimbledon FC | - | Tottenham Hotspur | 5:1 |  |
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| 36. Round | 19/04/1991 | Sheffield United | - | Tottenham Hotspur | 2:2 | ||||
| 35. Round | 19/05/1991 | Manchester United | - | Tottenham Hotspur | 1:1 |
Iceland