| 1. Round | 24/08/1990 | Chelsea FC | - | Derby County | 2:1 | ||||
| 2. Round | 27/08/1990 | Crystal Palace | - | Chelsea FC | 2:1 | ||||
| 4. Round | 07/09/1990 | Chelsea FC | - | Sunderland AFC | 3:2 | ||||
| 5. Round | 14/09/1990 | Arsenal FC | - | Chelsea FC | 4:1 | ||||
| 6. Round | 21/09/1990 | Chelsea FC | - | Manchester City | 1:1 | ||||
| 9. Round | 20/10/1990 | Chelsea FC | - | Nottingham Forest | 0:0 | ||||
| 10. Round | 27/10/1990 | Liverpool FC | - | Chelsea FC | 2:0 | ||||
| 20. Round | 28/12/1990 | Luton Town | - | Chelsea FC | 2:0 | ||||
| 21. Round | 31/12/1990 | Chelsea FC | - | Everton FC | 1:2 | ||||
| 25. Round | 08/02/1991 | Manchester City | - | Chelsea FC | 2:1 | ||||
| 28. Round | 01/03/1991 | Tottenham Hotspur | - | Chelsea FC | 1:1 | ||||
| 29. Round | 08/03/1991 | Chelsea FC | - | Manchester United | 3:2 | ||||
| 30. Round | 15/03/1991 | Sheffield United | - | Chelsea FC | 1:0 |
Scotland