| 2. Runde | 26.09.1990 | Walsall FC | - | Chelsea FC | 0:5 |  |
|||
| 2. Runde | 10.10.1990 | Chelsea FC | - | Walsall FC | 4:1 | ||||
| 3. Runde | 31.10.1990 | Chelsea FC | - | Portsmouth FC | 0:0 | ||||
| 3. Runde | 06.11.1990 | Portsmouth FC | - | Chelsea FC | 2:3 | |
|||
| Achtelfinale | 28.11.1990 | Oxford United | - | Chelsea FC | 1:2 |
England