| 2. Round | 26/09/1990 | Walsall FC | - | Chelsea FC | 0:5 | ||||
| 2. Round | 10/10/1990 | Chelsea FC | - | Walsall FC | 4:1 |  |
|||
| 3. Round | 31/10/1990 | Chelsea FC | - | Portsmouth FC | 0:0 | ||||
| 3. Round | 06/11/1990 | Portsmouth FC | - | Chelsea FC | 2:3 | ||||
| Round of 16 | 28/11/1990 | Oxford United | - | Chelsea FC | 1:2 | ||||
| Quarter-finals | 16/01/1991 | Chelsea FC | - | Tottenham Hotspur | 0:0 | ||||
| Semi-finals | 24/02/1991 | Chelsea FC | - | Sheffield Wednesday | 0:2 |  |
England