| 1. Round | 18/08/1996 | Southampton FC | - | Chelsea FC | 0:0 | ||||
| 2. Round | 21/08/1996 | Chelsea FC | - | Middlesbrough FC | 1:0 | ||||
| 3. Round | 24/08/1996 | Chelsea FC | - | Coventry City | 2:0 | ||||
| 4. Round | 04/09/1996 | Arsenal FC | - | Chelsea FC | 3:3 | ||||
| 5. Round | 07/09/1996 | Sheffield Wednesday | - | Chelsea FC | 0:2 |
Russia