| 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 | ||||
| 6. Round | 15/09/1996 | Chelsea FC | - | Aston Villa | 1:1 | ||||
| 7. Round | 21/09/1996 | Liverpool FC | - | Chelsea FC | 5:1 | ||||
| 29. Round | 01/03/1997 | Derby County | - | Chelsea FC | 3:2 | ||||
| 27. Round | 05/03/1997 | Chelsea FC | - | Blackburn Rovers | 1:1 | ||||
| 33. Round | 05/04/1997 | Chelsea FC | - | Arsenal FC | 0:3 | ||||
| 26. Round | 16/04/1997 | Newcastle United | - | Chelsea FC | 3:1 | ||||
| 35. Round | 19/04/1997 | Chelsea FC | - | Leicester City | 2:1 | ||||
| 36. Round | 22/04/1997 | Wimbledon FC | - | Chelsea FC | 0:1 | ||||
| 37. Round | 03/05/1997 | Chelsea FC | - | Leeds United | 0:0 |
England