| 2. Round | 26/09/1990 | Tottenham Hotspur | - | Hartlepool United | 5:0 | ||||
| 2. Round | 09/10/1990 | Hartlepool United | - | Tottenham Hotspur | 1:2 |  |
|||
| 3. Round | 30/10/1990 | Tottenham Hotspur | - | Bradford City | 2:1 | |
|||
| Round of 16 | 26/11/1990 | Sheffield United | - | Tottenham Hotspur | 0:2 | |
|||
| Quarter-finals | 16/01/1991 | Chelsea FC | - | Tottenham Hotspur | 0:0 | ||||
| Quarter-finals | 23/01/1991 | Tottenham Hotspur | - | Chelsea FC | 0:3 |
England