| 5. Round | 14/09/1990 | Arsenal FC | - | Chelsea FC | 4:1 | ||||
| 20. Round | 28/12/1990 | Luton Town | - | Chelsea FC | 2:0 | ||||
| 25. Round | 08/02/1991 | Manchester City | - | Chelsea FC | 2:1 | ||||
| 26. Round | 15/02/1991 | Chelsea FC | - | Wimbledon FC | 0:0 | ||||
| 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 | ||||
| 31. Round | 22/03/1991 | Chelsea FC | - | Southampton FC | 0:2 | ||||
| 32. Round | 29/03/1991 | Chelsea FC | - | Leeds United | 1:2 | ||||
| 33. Round | 31/03/1991 | Coventry City | - | Chelsea FC | 1:0 | ||||
| 34. Round | 05/04/1991 | Chelsea FC | - | Luton Town | 3:3 | ||||
| 35. Round | 12/04/1991 | Everton FC | - | Chelsea FC | 2:2 | ||||
| 27. Round | 15/04/1991 | Norwich City | - | Chelsea FC | 1:3 | ||||
| 36. Round | 19/04/1991 | Nottingham Forest | - | Chelsea FC | 7:0 | ||||
| 37. Round | 03/05/1991 | Chelsea FC | - | Liverpool FC | 4:2 | ||||
| 38. Round | 10/05/1991 | Aston Villa | - | Chelsea FC | 2:2 |
England