| 5. Round | 07/09/1996 | Sheffield Wednesday | - | Chelsea FC | 0:2 | ||||
| 6. Round | 15/09/1996 | Chelsea FC | - | Aston Villa | 1:1 | ||||
| 7. Round | 21/09/1996 | Liverpool FC | - | Chelsea FC | 5:1 | ||||
| 8. Round | 28/09/1996 | Chelsea FC | - | Nottingham Forest | 1:1 | ||||
| 9. Round | 12/10/1996 | Leicester City | - | Chelsea FC | 1:3 | ||||
| 10. Round | 19/10/1996 | Chelsea FC | - | Wimbledon FC | 2:4 | ||||
| 11. Round | 26/10/1996 | Chelsea FC | - | Tottenham Hotspur | 3:1 | ||||
| 12. Round | 02/11/1996 | Manchester United | - | Chelsea FC | 1:2 | ||||
| 23. Round | 18/01/1997 | Chelsea FC | - | Derby County | 3:1 | ||||
| 25. Round | 01/02/1997 | Tottenham Hotspur | - | Chelsea FC | 1:2 | ||||
| 28. Round | 22/02/1997 | Chelsea FC | - | Manchester United | 1:1 | ||||
| 38. Round | 11/05/1997 | Everton FC | - | Chelsea FC | 1:2 |
England